# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
Di-ethylammonium-1,1'-binaphthyl-2,2'-dicarboxylate 
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 N2 O4'
_chemical_formula_weight         488.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.416(4)
_cell_length_b                   11.358(2)
_cell_length_c                   13.740(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.41(3)
_cell_angle_gamma                90.00
_cell_volume                     2715.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11557
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ scans and ω scans'
_diffrn_reflns_number            3282
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3282
_reflns_number_gt                2730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0505P)²+1.1439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49803(4) 0.19410(6) 0.09140(5) 0.03068(19) Uani 1 1 d . . .
C1 C 0.45689(5) 0.34606(8) 0.25303(6) 0.01986(19) Uani 1 1 d . . .
C10 C 0.34138(5) 0.44077(8) 0.31751(7) 0.0243(2) Uani 1 1 d . . .
O2 O 0.39907(5) 0.07997(7) 0.12912(6) 0.0369(2) Uani 1 1 d . . .
C9 C 0.42284(5) 0.43340(8) 0.31368(7) 0.0222(2) Uani 1 1 d . . .
C2 C 0.40931(5) 0.26798(8) 0.20203(7) 0.02123(19) Uani 1 1 d . . .
C3 C 0.32828(6) 0.27502(9) 0.20887(7) 0.0263(2) Uani 1 1 d . . .
H3 H 0.2965 0.2195 0.1747 0.032 Uiso 1 1 calc R . .
C8 C 0.46749(6) 0.51316(9) 0.37166(8) 0.0297(2) Uani 1 1 d . . .
H8 H 0.5219 0.5104 0.3701 0.036 Uiso 1 1 calc R . .
C4 C 0.29520(6) 0.35996(9) 0.26348(7) 0.0275(2) Uani 1 1 d . . .
H4 H 0.2408 0.3647 0.2651 0.033 Uiso 1 1 calc R . .
C11 C 0.43839(6) 0.17260(8) 0.13616(7) 0.0242(2) Uani 1 1 d . . .
C5 C 0.30791(6) 0.52788(9) 0.37688(8) 0.0320(2) Uani 1 1 d . . .
H5 H 0.2536 0.5343 0.3780 0.038 Uiso 1 1 calc R . .
C6 C 0.35306(7) 0.60224(10) 0.43209(9) 0.0386(3) Uani 1 1 d . . .
H6 H 0.3301 0.6595 0.4721 0.046 Uiso 1 1 calc R . .
C7 C 0.43342(7) 0.59443(10) 0.43001(9) 0.0376(3) Uani 1 1 d . . .
H7 H 0.4645 0.6458 0.4694 0.045 Uiso 1 1 calc R . .
N1A N 0.61193(5) 0.06852(8) 0.02752(7) 0.0311(2) Uani 1 1 d . . .
C3A C 0.66412(7) 0.16595(11) 0.00049(9) 0.0395(3) Uani 1 1 d . . .
H3A2 H 0.7134 0.1326 -0.0199 0.047 Uiso 1 1 calc R . .
H3A1 H 0.6750 0.2167 0.0580 0.047 Uiso 1 1 calc R . .
C1A C 0.64237(8) -0.00424(12) 0.11028(9) 0.0439(3) Uani 1 1 d . . .
H1A1 H 0.6562 0.0472 0.1665 0.053 Uiso 1 1 calc R . .
H1A2 H 0.6894 -0.0459 0.0913 0.053 Uiso 1 1 calc R . .
C4A C 0.62887(8) 0.23850(14) -0.08074(12) 0.0543(4) Uani 1 1 d . . .
H4A2 H 0.6150 0.1874 -0.1362 0.081 Uiso 1 1 calc R . .
H4A3 H 0.6659 0.2978 -0.1007 0.081 Uiso 1 1 calc R . .
H4A1 H 0.5827 0.2777 -0.0584 0.081 Uiso 1 1 calc R . .
C2A C 0.58289(9) -0.09249(12) 0.13892(10) 0.0495(3) Uani 1 1 d . . .
H2A1 H 0.5382 -0.0510 0.1631 0.074 Uiso 1 1 calc R . .
H2A2 H 0.6048 -0.1439 0.1902 0.074 Uiso 1 1 calc R . .
H2A3 H 0.5670 -0.1400 0.0821 0.074 Uiso 1 1 calc R . .
H1 H 0.5633(8) 0.1031(12) 0.0475(10) 0.041(4) Uiso 1 1 d . . .
H2 H 0.6014(9) 0.0197(14) -0.0245(12) 0.049(4) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2532(13) . ?
C1 C2 1.3840(13) . ?
C1 C9 1.4393(13) . ?
C1 C1 1.5073(17) 2_655 ?
C10 C4 1.4107(15) . ?
C10 C5 1.4227(13) . ?
C10 C9 1.4242(14) . ?
O2 C11 1.2568(12) . ?
C9 C8 1.4171(14) . ?
C2 C3 1.4206(14) . ?
C2 C11 1.5126(13) . ?
C3 C4 1.3646(14) . ?
C3 H3 0.9500 . ?
C8 C7 1.3737(15) . ?
C8 H8 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.3628(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4037(17) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1A C1A 1.4855(16) . ?
N1A C3A 1.4891(15) . ?
N1A H1 0.982(14) . ?
N1A H2 0.917(16) . ?
C3A C4A 1.498(2) . ?
C3A H3A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C1A C2A 1.506(2) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
C4A H4A1 0.9800 . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 118.83(8) . . ?
C2 C1 C1 123.27(8) . 2_655 ?
C9 C1 C1 117.89(8) . 2_655 ?
C4 C10 C5 121.05(9) . . ?
C4 C10 C9 119.28(9) . . ?
C5 C10 C9 119.66(9) . . ?
C8 C9 C10 117.75(9) . . ?
C8 C9 C1 122.43(9) . . ?
C10 C9 C1 119.82(9) . . ?
C1 C2 C3 120.39(8) . . ?
C1 C2 C11 123.61(8) . . ?
C3 C2 C11 116.00(8) . . ?
C4 C3 C2 121.31(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C7 C8 C9 121.16(10) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C3 C4 C10 120.32(9) . . ?
C3 C4 H4 119.8 . . ?
C10 C4 H4 119.8 . . ?
O1 C11 O2 125.84(9) . . ?
O1 C11 C2 117.34(8) . . ?
O2 C11 C2 116.79(9) . . ?
C6 C5 C10 120.62(10) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 120.13(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.65(11) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C1A N1A C3A 113.73(9) . . ?
C1A N1A H1 107.0(8) . . ?
C3A N1A H1 108.4(8) . . ?
C1A N1A H2 108.3(10) . . ?
C3A N1A H2 111.0(9) . . ?
H1 N1A H2 108.3(13) . . ?
N1A C3A C4A 111.06(10) . . ?
N1A C3A H3A2 109.4 . . ?
C4A C3A H3A2 109.4 . . ?
N1A C3A H3A1 109.4 . . ?
C4A C3A H3A1 109.4 . . ?
H3A2 C3A H3A1 108.0 . . ?
N1A C1A C2A 110.06(10) . . ?
N1A C1A H1A1 109.6 . . ?
C2A C1A H1A1 109.6 . . ?
N1A C1A H1A2 109.6 . . ?
C2A C1A H1A2 109.6 . . ?
H1A1 C1A H1A2 108.2 . . ?
C3A C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C3A C4A H4A1 109.5 . . ?
H4A2 C4A H4A1 109.5 . . ?
H4A3 C4A H4A1 109.5 . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C10 C9 C8 -177.71(9) . . . . ?
C5 C10 C9 C8 1.19(14) . . . . ?
C4 C10 C9 C1 1.64(14) . . . . ?
C5 C10 C9 C1 -179.46(9) . . . . ?
C2 C1 C9 C8 177.09(9) . . . . ?
C1 C1 C9 C8 -4.05(14) 2_655 . . . ?
C2 C1 C9 C10 -2.23(13) . . . . ?
C1 C1 C9 C10 176.63(8) 2_655 . . . ?
C9 C1 C2 C3 0.63(13) . . . . ?
C1 C1 C2 C3 -178.15(9) 2_655 . . . ?
C9 C1 C2 C11 -179.98(8) . . . . ?
C1 C1 C2 C11 1.23(14) 2_655 . . . ?
C1 C2 C3 C4 1.62(14) . . . . ?
C11 C2 C3 C4 -177.81(9) . . . . ?
C10 C9 C8 C7 0.35(15) . . . . ?
C1 C9 C8 C7 -178.98(10) . . . . ?
C2 C3 C4 C10 -2.24(15) . . . . ?
C5 C10 C4 C3 -178.30(9) . . . . ?
C9 C10 C4 C3 0.59(14) . . . . ?
C1 C2 C11 O1 -32.84(13) . . . . ?
C3 C2 C11 O1 146.57(9) . . . . ?
C1 C2 C11 O2 149.20(9) . . . . ?
C3 C2 C11 O2 -31.39(13) . . . . ?
C4 C10 C5 C6 177.13(10) . . . . ?
C9 C10 C5 C6 -1.75(15) . . . . ?
C10 C5 C6 C7 0.74(17) . . . . ?
C9 C8 C7 C6 -1.39(18) . . . . ?
C5 C6 C7 C8 0.84(19) . . . . ?
C1A N1A C3A C4A -177.88(10) . . . . ?
C3A N1A C1A C2A 174.42(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 969502'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Di-n-butylammonium-1,1'-binaphthyl-2,2'-dicarboxylate 
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H52 N2 O4'
_chemical_formula_weight         600.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5427(19)
_cell_length_b                   12.417(3)
_cell_length_c                   15.396(3)
_cell_angle_alpha                81.62(3)
_cell_angle_beta                 79.45(3)
_cell_angle_gamma                75.37(3)
_cell_volume                     1725.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15256
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 none 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7580
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.15
_reflns_number_total             7580
_reflns_number_gt                5725
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0607P)²+0.3764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7580
_refine_ls_number_parameters     429
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2' O 0.81423(10) 0.67903(8) 0.07596(6) 0.0377(2) Uani 1 1 d . . .
O1' O 0.99989(10) 0.58375(8) 0.14643(6) 0.0363(2) Uani 1 1 d . . .
O2 O 1.03273(11) 0.62819(8) 0.37134(6) 0.0380(2) Uani 1 1 d . . .
C9' C 0.92272(13) 0.87556(10) 0.28923(8) 0.0240(3) Uani 1 1 d . . .
C1' C 0.96817(12) 0.78971(9) 0.22979(8) 0.0216(2) Uani 1 1 d . . .
C10 C 1.35858(13) 0.77742(11) 0.10839(8) 0.0263(3) Uani 1 1 d . . .
C9 C 1.20347(13) 0.81134(10) 0.13309(8) 0.0240(3) Uani 1 1 d . . .
C1 C 1.13013(12) 0.74621(10) 0.20339(8) 0.0218(2) Uani 1 1 d . . .
C2 C 1.21135(13) 0.65135(10) 0.24554(8) 0.0238(3) Uani 1 1 d . . .
C2' C 0.86354(13) 0.75926(10) 0.19344(8) 0.0247(3) Uani 1 1 d . . .
C4 C 1.43660(13) 0.67860(11) 0.15211(8) 0.0281(3) Uani 1 1 d . . .
H4 H 1.5397 0.6547 0.1357 0.034 Uiso 1 1 calc R . .
C11' C 0.89723(13) 0.66656(10) 0.13358(8) 0.0263(3) Uani 1 1 d . . .
N1A N 1.11064(12) 0.34314(9) 0.46343(7) 0.0327(3) Uani 1 1 d D B .
C3 C 1.36454(13) 0.61732(11) 0.21785(8) 0.0268(3) Uani 1 1 d . . .
H3 H 1.4183 0.5502 0.2457 0.032 Uiso 1 1 calc R . .
O1 O 1.21277(12) 0.48111(9) 0.33554(8) 0.0550(3) Uani 1 1 d . . .
C8' C 1.02466(14) 0.90929(11) 0.32950(8) 0.0294(3) Uani 1 1 d . . .
H8' H 1.1263 0.8765 0.3155 0.035 Uiso 1 1 calc R . .
C10' C 0.77204(14) 0.92798(10) 0.30986(8) 0.0277(3) Uani 1 1 d . . .
C11 C 1.14543(14) 0.58182(11) 0.32353(9) 0.0294(3) Uani 1 1 d . . .
C3' C 0.71390(14) 0.81589(11) 0.21263(9) 0.0311(3) Uani 1 1 d . . .
H3' H 0.6432 0.7967 0.1854 0.037 Uiso 1 1 calc R . .
C8 C 1.12817(15) 0.91145(11) 0.08866(9) 0.0307(3) Uani 1 1 d . . .
H8 H 1.0250 0.9358 0.1042 0.037 Uiso 1 1 calc R . .
C6' C 0.82956(16) 1.03878(11) 0.40971(9) 0.0365(3) Uani 1 1 d . . .
H6' H 0.7987 1.0929 0.4512 0.044 Uiso 1 1 calc R . .
C4' C 0.66948(14) 0.89684(11) 0.26894(9) 0.0333(3) Uani 1 1 d . . .
H4' H 0.5686 0.9328 0.2809 0.040 Uiso 1 1 calc R . .
C6 C 1.35358(16) 0.93920(13) -0.00097(9) 0.0381(3) Uani 1 1 d . . .
H6 H 1.4032 0.9821 -0.0469 0.046 Uiso 1 1 calc R . .
C7' C 0.97879(16) 0.98849(11) 0.38834(9) 0.0347(3) Uani 1 1 d . . .
H7' H 1.0488 1.0095 0.4149 0.042 Uiso 1 1 calc R . .
C5 C 1.43054(15) 0.84417(12) 0.04080(9) 0.0333(3) Uani 1 1 d . . .
H5 H 1.5338 0.8223 0.0244 0.040 Uiso 1 1 calc R . .
C7 C 1.20135(16) 0.97383(12) 0.02367(9) 0.0376(3) Uani 1 1 d . . .
H7 H 1.1486 1.0409 -0.0049 0.045 Uiso 1 1 calc R . .
C5' C 0.72875(15) 1.00987(11) 0.37086(9) 0.0342(3) Uani 1 1 d . . .
H5' H 0.6279 1.0451 0.3849 0.041 Uiso 1 1 calc R . .
C1A C 1.24995(15) 0.26180(11) 0.47769(9) 0.0336(3) Uani 1 1 d . . .
H1A1 H 1.3072 0.2420 0.4194 0.040 Uiso 1 1 calc R . .
H1A2 H 1.2278 0.1926 0.5119 0.040 Uiso 1 1 calc R . .
C2A C 1.34095(16) 0.30815(13) 0.52703(10) 0.0400(3) Uani 1 1 d . . .
H2A1 H 1.2918 0.3151 0.5891 0.048 Uiso 1 1 calc R . .
H2A2 H 1.3482 0.3839 0.4988 0.048 Uiso 1 1 calc R . .
C3A C 1.49425(16) 0.23339(15) 0.52703(11) 0.0470(4) Uani 1 1 d . . .
H3A1 H 1.4863 0.1558 0.5490 0.056 Uiso 1 1 calc R . .
H3A2 H 1.5466 0.2330 0.4653 0.056 Uiso 1 1 calc R . .
C5A C 1.01299(18) 0.29578(16) 0.42414(11) 0.0521(4) Uani 1 1 d . . .
H5A1 H 1.0135 0.2214 0.4578 0.063 Uiso 1 1 calc R A 1
H5A2 H 1.0640 0.2812 0.3635 0.063 Uiso 1 1 calc R A 1
C7A C 0.7991(3) 0.3617(2) 0.3434(2) 0.0616(10) Uani 0.648(4) 1 d P B 2
H7A1 H 0.7714 0.2912 0.3703 0.074 Uiso 0.648(4) 1 calc PR B 2
H7A2 H 0.8631 0.3468 0.2861 0.074 Uiso 0.648(4) 1 calc PR B 2
C4A C 1.58352(19) 0.27071(19) 0.58415(14) 0.0649(5) Uani 1 1 d . . .
H4A1 H 1.5903 0.3479 0.5635 0.097 Uiso 1 1 calc R . .
H4A2 H 1.6821 0.2217 0.5797 0.097 Uiso 1 1 calc R . .
H4A3 H 1.5357 0.2666 0.6462 0.097 Uiso 1 1 calc R . .
C6A C 0.8837(3) 0.3952(2) 0.40334(19) 0.0374(7) Uani 0.648(4) 1 d P B 2
H6A1 H 0.8188 0.4163 0.4592 0.045 Uiso 0.648(4) 1 calc PR B 2
H6A2 H 0.9218 0.4608 0.3743 0.045 Uiso 0.648(4) 1 calc PR B 2
N1B N 0.79258(11) 0.53959(9) -0.03701(7) 0.0278(2) Uani 1 1 d D . .
C5B C 0.69848(15) 0.61664(11) -0.09813(9) 0.0329(3) Uani 1 1 d . . .
H5B1 H 0.5999 0.6444 -0.0647 0.039 Uiso 1 1 calc R . .
H5B2 H 0.6875 0.5749 -0.1456 0.039 Uiso 1 1 calc R . .
C1B C 0.72313(14) 0.44955(11) 0.01280(9) 0.0325(3) Uani 1 1 d . . .
H1B1 H 0.6963 0.4086 -0.0298 0.039 Uiso 1 1 calc R . .
H1B2 H 0.6321 0.4836 0.0510 0.039 Uiso 1 1 calc R . .
C2B C 0.82452(15) 0.36799(12) 0.06990(9) 0.0346(3) Uani 1 1 d . . .
H2B1 H 0.8472 0.4081 0.1147 0.042 Uiso 1 1 calc R . .
H2B2 H 0.9177 0.3367 0.0322 0.042 Uiso 1 1 calc R . .
C6B C 0.76257(15) 0.71493(12) -0.13957(9) 0.0352(3) Uani 1 1 d . . .
H6B1 H 0.8618 0.6870 -0.1722 0.042 Uiso 1 1 calc R . .
H6B2 H 0.7724 0.7571 -0.0920 0.042 Uiso 1 1 calc R . .
C7B C 0.66829(17) 0.79326(13) -0.20307(10) 0.0436(4) Uani 1 1 d . . .
H7B1 H 0.6651 0.7526 -0.2531 0.052 Uiso 1 1 calc R . .
H7B2 H 0.5670 0.8162 -0.1716 0.052 Uiso 1 1 calc R . .
C3B C 0.75579(18) 0.27321(13) 0.11671(11) 0.0445(4) Uani 1 1 d . . .
H3B1 H 0.6720 0.3035 0.1616 0.053 Uiso 1 1 calc R . .
H3B2 H 0.7172 0.2423 0.0728 0.053 Uiso 1 1 calc R . .
C8B C 0.7251(2) 0.89702(15) -0.23959(12) 0.0558(4) Uani 1 1 d . . .
H8B1 H 0.8288 0.8749 -0.2650 0.084 Uiso 1 1 calc R . .
H8B2 H 0.7142 0.9437 -0.1915 0.084 Uiso 1 1 calc R . .
H8B3 H 0.6689 0.9395 -0.2859 0.084 Uiso 1 1 calc R . .
C4B C 0.8620(2) 0.17980(16) 0.16193(14) 0.0695(6) Uani 1 1 d . . .
H4B1 H 0.8982 0.2093 0.2070 0.104 Uiso 1 1 calc R . .
H4B2 H 0.9446 0.1487 0.1177 0.104 Uiso 1 1 calc R . .
H4B3 H 0.8119 0.1209 0.1904 0.104 Uiso 1 1 calc R . .
H2' H 0.8791 0.5006 -0.0737 0.040(4) Uiso 1 1 d R . .
H1' H 0.8211 0.5796 0.0035 0.049(5) Uiso 1 1 d RD . .
C7A' C 0.8588(5) 0.4312(4) 0.3297(3) 0.0405(13) Uiso 0.352(4) 1 d P B 1
H7A3 H 0.9017 0.4923 0.3396 0.049 Uiso 0.352(4) 1 calc PR B 1
H7A4 H 0.9229 0.3925 0.2798 0.049 Uiso 0.352(4) 1 calc PR B 1
C8A' C 0.7061(8) 0.4816(6) 0.3041(5) 0.0417(15) Uani 0.352(4) 1 d P B 1
H8A1 H 0.6648 0.4217 0.2916 0.062 Uiso 0.352(4) 1 calc PR B 1
H8A2 H 0.7136 0.5352 0.2510 0.062 Uiso 0.352(4) 1 calc PR B 1
H8A3 H 0.6422 0.5199 0.3532 0.062 Uiso 0.352(4) 1 calc PR B 1
C8A C 0.6629(6) 0.4483(4) 0.3259(5) 0.094(2) Uani 0.648(4) 1 d P B 2
H8A4 H 0.5998 0.4651 0.3824 0.141 Uiso 0.648(4) 1 calc PR B 2
H8A5 H 0.6102 0.4196 0.2888 0.141 Uiso 0.648(4) 1 calc PR B 2
H8A6 H 0.6898 0.5167 0.2950 0.141 Uiso 0.648(4) 1 calc PR B 2
C6A' C 0.8553(5) 0.3473(3) 0.4143(3) 0.0423(14) Uani 0.352(4) 1 d P B 1
H6A3 H 0.8034 0.3863 0.4668 0.051 Uiso 0.352(4) 1 calc PR B 1
H6A4 H 0.8047 0.2891 0.4079 0.051 Uiso 0.352(4) 1 calc PR B 1
H1 H 1.0616 0.3620 0.5181 0.038(4) Uiso 1 1 d R . .
H2 H 1.1388 0.4032 0.4222 0.057(5) Uiso 1 1 d RD . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2' C11' 1.2623(15) . ?
O1' C11' 1.2486(16) . ?
O2 C11 1.2453(16) . ?
C9' C8' 1.4171(17) . ?
C9' C10' 1.4186(17) . ?
C9' C1' 1.4378(17) . ?
C1' C2' 1.3820(17) . ?
C1' C1 1.5026(16) . ?
C10 C4 1.4123(19) . ?
C10 C5 1.4198(19) . ?
C10 C9 1.4278(17) . ?
C9 C8 1.4179(18) . ?
C9 C1 1.4383(17) . ?
C1 C2 1.3818(17) . ?
C2 C3 1.4176(17) . ?
C2 C11 1.5096(18) . ?
C2' C3' 1.4212(17) . ?
C2' C11' 1.5139(17) . ?
C4 C3 1.3643(19) . ?
C4 H4 0.9500 . ?
N1A C5A 1.472(2) . ?
N1A C1A 1.4831(17) . ?
N1A H1 0.9163 . ?
N1A H2 0.9654 . ?
C3 H3 0.9500 . ?
O1 C11 1.2575(17) . ?
C8' C7' 1.3698(19) . ?
C8' H8' 0.9500 . ?
C10' C4' 1.4115(18) . ?
C10' C5' 1.4180(19) . ?
C3' C4' 1.3585(19) . ?
C3' H3' 0.9500 . ?
C8 C7 1.3712(19) . ?
C8 H8 0.9500 . ?
C6' C5' 1.364(2) . ?
C6' C7' 1.402(2) . ?
C6' H6' 0.9500 . ?
C4' H4' 0.9500 . ?
C6 C5 1.364(2) . ?
C6 C7 1.403(2) . ?
C6 H6 0.9500 . ?
C7' H7' 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C5' H5' 0.9500 . ?
C1A C2A 1.511(2) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A C3A 1.522(2) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.519(2) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C5A C6A' 1.505(5) . ?
C5A C6A 1.552(3) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C7A C6A 1.493(4) . ?
C7A C8A 1.502(6) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
N1B C1B 1.4884(18) . ?
N1B C5B 1.4900(17) . ?
N1B H2' 0.9706 . ?
N1B H1' 0.9641 . ?
C5B C6B 1.509(2) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C1B C2B 1.514(2) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B C3B 1.518(2) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C6B C7B 1.521(2) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B C8B 1.516(2) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C3B C4B 1.512(2) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
C4B H4B3 0.9800 . ?
C7A' C8A' 1.533(9) . ?
C7A' C6A' 1.546(5) . ?
C7A' H7A3 0.9900 . ?
C7A' H7A4 0.9900 . ?
C8A' H8A1 0.9800 . ?
C8A' H8A2 0.9800 . ?
C8A' H8A3 0.9800 . ?
C8A H8A4 0.9800 . ?
C8A H8A5 0.9800 . ?
C8A H8A6 0.9800 . ?
C6A' H6A3 0.9900 . ?
C6A' H6A4 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8' C9' C10' 118.20(11) . . ?
C8' C9' C1' 121.80(11) . . ?
C10' C9' C1' 120.00(11) . . ?
C2' C1' C9' 119.21(11) . . ?
C2' C1' C1 123.31(10) . . ?
C9' C1' C1 117.18(10) . . ?
C4 C10 C5 121.68(12) . . ?
C4 C10 C9 119.15(11) . . ?
C5 C10 C9 119.17(12) . . ?
C8 C9 C10 117.92(11) . . ?
C8 C9 C1 122.43(11) . . ?
C10 C9 C1 119.61(11) . . ?
C2 C1 C9 119.23(11) . . ?
C2 C1 C1' 123.62(11) . . ?
C9 C1 C1' 117.08(10) . . ?
C1 C2 C3 120.12(11) . . ?
C1 C2 C11 122.95(11) . . ?
C3 C2 C11 116.90(11) . . ?
C1' C2' C3' 119.67(11) . . ?
C1' C2' C11' 124.00(11) . . ?
C3' C2' C11' 116.33(11) . . ?
C3 C4 C10 120.25(11) . . ?
C3 C4 H4 119.9 . . ?
C10 C4 H4 119.9 . . ?
O1' C11' O2' 125.59(12) . . ?
O1' C11' C2' 118.40(11) . . ?
O2' C11' C2' 115.97(11) . . ?
C5A N1A C1A 112.97(11) . . ?
C5A N1A H1 106.4 . . ?
C1A N1A H1 107.4 . . ?
C5A N1A H2 108.6 . . ?
C1A N1A H2 105.4 . . ?
H1 N1A H2 116.3 . . ?
C4 C3 C2 121.60(12) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C7' C8' C9' 120.96(12) . . ?
C7' C8' H8' 119.5 . . ?
C9' C8' H8' 119.5 . . ?
C4' C10' C5' 121.93(12) . . ?
C4' C10' C9' 118.86(11) . . ?
C5' C10' C9' 119.22(12) . . ?
O2 C11 O1 125.55(13) . . ?
O2 C11 C2 118.37(11) . . ?
O1 C11 C2 116.06(12) . . ?
C4' C3' C2' 121.65(12) . . ?
C4' C3' H3' 119.2 . . ?
C2' C3' H3' 119.2 . . ?
C7 C8 C9 121.30(13) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C5' C6' C7' 119.88(12) . . ?
C5' C6' H6' 120.1 . . ?
C7' C6' H6' 120.1 . . ?
C3' C4' C10' 120.54(12) . . ?
C3' C4' H4' 119.7 . . ?
C10' C4' H4' 119.7 . . ?
C5 C6 C7 120.20(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8' C7' C6' 120.68(13) . . ?
C8' C7' H7' 119.7 . . ?
C6' C7' H7' 119.7 . . ?
C6 C5 C10 120.97(13) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C8 C7 C6 120.43(13) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C6' C5' C10' 121.03(13) . . ?
C6' C5' H5' 119.5 . . ?
C10' C5' H5' 119.5 . . ?
N1A C1A C2A 111.95(11) . . ?
N1A C1A H1A1 109.2 . . ?
C2A C1A H1A1 109.2 . . ?
N1A C1A H1A2 109.2 . . ?
C2A C1A H1A2 109.2 . . ?
H1A1 C1A H1A2 107.9 . . ?
C1A C2A C3A 111.58(12) . . ?
C1A C2A H2A1 109.3 . . ?
C3A C2A H2A1 109.3 . . ?
C1A C2A H2A2 109.3 . . ?
C3A C2A H2A2 109.3 . . ?
H2A1 C2A H2A2 108.0 . . ?
C4A C3A C2A 113.03(14) . . ?
C4A C3A H3A1 109.0 . . ?
C2A C3A H3A1 109.0 . . ?
C4A C3A H3A2 109.0 . . ?
C2A C3A H3A2 109.0 . . ?
H3A1 C3A H3A2 107.8 . . ?
N1A C5A C6A' 127.2(2) . . ?
N1A C5A C6A 105.75(16) . . ?
C6A' C5A C6A 26.45(12) . . ?
N1A C5A H5A1 105.5 . . ?
C6A' C5A H5A1 105.5 . . ?
C6A C5A H5A1 130.7 . . ?
N1A C5A H5A2 105.5 . . ?
C6A' C5A H5A2 105.5 . . ?
C6A C5A H5A2 101.0 . . ?
H5A1 C5A H5A2 106.1 . . ?
C6A C7A C8A 113.7(3) . . ?
C6A C7A H7A1 108.8 . . ?
C8A C7A H7A1 108.8 . . ?
C6A C7A H7A2 108.8 . . ?
C8A C7A H7A2 108.8 . . ?
H7A1 C7A H7A2 107.7 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C7A C6A C5A 109.3(2) . . ?
C7A C6A H6A1 109.8 . . ?
C5A C6A H6A1 109.8 . . ?
C7A C6A H6A2 109.8 . . ?
C5A C6A H6A2 109.8 . . ?
H6A1 C6A H6A2 108.3 . . ?
C1B N1B C5B 112.66(10) . . ?
C1B N1B H2' 104.8 . . ?
C5B N1B H2' 107.1 . . ?
C1B N1B H1' 110.4 . . ?
C5B N1B H1' 111.8 . . ?
H2' N1B H1' 109.7 . . ?
N1B C5B C6B 111.74(11) . . ?
N1B C5B H5B1 109.3 . . ?
C6B C5B H5B1 109.3 . . ?
N1B C5B H5B2 109.3 . . ?
C6B C5B H5B2 109.3 . . ?
H5B1 C5B H5B2 107.9 . . ?
N1B C1B C2B 111.74(11) . . ?
N1B C1B H1B1 109.3 . . ?
C2B C1B H1B1 109.3 . . ?
N1B C1B H1B2 109.3 . . ?
C2B C1B H1B2 109.3 . . ?
H1B1 C1B H1B2 107.9 . . ?
C1B C2B C3B 111.34(12) . . ?
C1B C2B H2B1 109.4 . . ?
C3B C2B H2B1 109.4 . . ?
C1B C2B H2B2 109.4 . . ?
C3B C2B H2B2 109.4 . . ?
H2B1 C2B H2B2 108.0 . . ?
C5B C6B C7B 112.13(12) . . ?
C5B C6B H6B1 109.2 . . ?
C7B C6B H6B1 109.2 . . ?
C5B C6B H6B2 109.2 . . ?
C7B C6B H6B2 109.2 . . ?
H6B1 C6B H6B2 107.9 . . ?
C8B C7B C6B 112.63(13) . . ?
C8B C7B H7B1 109.1 . . ?
C6B C7B H7B1 109.1 . . ?
C8B C7B H7B2 109.1 . . ?
C6B C7B H7B2 109.1 . . ?
H7B1 C7B H7B2 107.8 . . ?
C4B C3B C2B 113.15(14) . . ?
C4B C3B H3B1 108.9 . . ?
C2B C3B H3B1 108.9 . . ?
C4B C3B H3B2 108.9 . . ?
C2B C3B H3B2 108.9 . . ?
H3B1 C3B H3B2 107.8 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C3B C4B H4B1 109.5 . . ?
C3B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C3B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C8A' C7A' C6A' 112.4(4) . . ?
C8A' C7A' H7A3 109.1 . . ?
C6A' C7A' H7A3 109.1 . . ?
C8A' C7A' H7A4 109.1 . . ?
C6A' C7A' H7A4 109.1 . . ?
H7A3 C7A' H7A4 107.8 . . ?
C7A C8A H8A4 109.5 . . ?
C7A C8A H8A5 109.5 . . ?
H8A4 C8A H8A5 109.5 . . ?
C7A C8A H8A6 109.5 . . ?
H8A4 C8A H8A6 109.5 . . ?
H8A5 C8A H8A6 109.5 . . ?
C5A C6A' C7A' 105.9(3) . . ?
C5A C6A' H6A3 110.6 . . ?
C7A' C6A' H6A3 110.6 . . ?
C5A C6A' H6A4 110.6 . . ?
C7A' C6A' H6A4 110.6 . . ?
H6A3 C6A' H6A4 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8' C9' C1' C2' 179.13(11) . . . . ?
C10' C9' C1' C2' -0.05(17) . . . . ?
C8' C9' C1' C1 -7.01(17) . . . . ?
C10' C9' C1' C1 173.81(11) . . . . ?
C4 C10 C9 C8 179.42(11) . . . . ?
C5 C10 C9 C8 -0.28(17) . . . . ?
C4 C10 C9 C1 1.64(17) . . . . ?
C5 C10 C9 C1 -178.06(11) . . . . ?
C8 C9 C1 C2 -178.02(11) . . . . ?
C10 C9 C1 C2 -0.34(16) . . . . ?
C8 C9 C1 C1' -1.04(16) . . . . ?
C10 C9 C1 C1' 176.64(10) . . . . ?
C2' C1' C1 C2 -91.12(15) . . . . ?
C9' C1' C1 C2 95.30(14) . . . . ?
C2' C1' C1 C9 92.04(14) . . . . ?
C9' C1' C1 C9 -81.54(13) . . . . ?
C9 C1 C2 C3 -1.75(17) . . . . ?
C1' C1 C2 C3 -178.52(11) . . . . ?
C9 C1 C2 C11 176.19(11) . . . . ?
C1' C1 C2 C11 -0.58(18) . . . . ?
C9' C1' C2' C3' 2.33(17) . . . . ?
C1 C1' C2' C3' -171.13(11) . . . . ?
C9' C1' C2' C11' -177.05(11) . . . . ?
C1 C1' C2' C11' 9.49(18) . . . . ?
C5 C10 C4 C3 178.87(11) . . . . ?
C9 C10 C4 C3 -0.82(17) . . . . ?
C1' C2' C11' O1' 32.87(18) . . . . ?
C3' C2' C11' O1' -146.53(12) . . . . ?
C1' C2' C11' O2' -149.26(12) . . . . ?
C3' C2' C11' O2' 31.33(16) . . . . ?
C10 C4 C3 C2 -1.31(18) . . . . ?
C1 C2 C3 C4 2.64(18) . . . . ?
C11 C2 C3 C4 -175.42(11) . . . . ?
C10' C9' C8' C7' 1.48(18) . . . . ?
C1' C9' C8' C7' -177.72(12) . . . . ?
C8' C9' C10' C4' 178.78(12) . . . . ?
C1' C9' C10' C4' -2.01(18) . . . . ?
C8' C9' C10' C5' -1.27(18) . . . . ?
C1' C9' C10' C5' 177.94(11) . . . . ?
C1 C2 C11 O2 -26.05(18) . . . . ?
C3 C2 C11 O2 151.95(12) . . . . ?
C1 C2 C11 O1 155.56(13) . . . . ?
C3 C2 C11 O1 -26.44(17) . . . . ?
C1' C2' C3' C4' -2.6(2) . . . . ?
C11' C2' C3' C4' 176.78(12) . . . . ?
C10 C9 C8 C7 0.28(18) . . . . ?
C1 C9 C8 C7 178.00(12) . . . . ?
C2' C3' C4' C10' 0.5(2) . . . . ?
C5' C10' C4' C3' -178.18(13) . . . . ?
C9' C10' C4' C3' 1.8(2) . . . . ?
C9' C8' C7' C6' -0.4(2) . . . . ?
C5' C6' C7' C8' -0.8(2) . . . . ?
C7 C6 C5 C10 1.3(2) . . . . ?
C4 C10 C5 C6 179.81(12) . . . . ?
C9 C10 C5 C6 -0.50(19) . . . . ?
C9 C8 C7 C6 0.5(2) . . . . ?
C5 C6 C7 C8 -1.3(2) . . . . ?
C7' C6' C5' C10' 1.0(2) . . . . ?
C4' C10' C5' C6' 179.99(13) . . . . ?
C9' C10' C5' C6' 0.0(2) . . . . ?
C5A N1A C1A C2A -173.81(12) . . . . ?
N1A C1A C2A C3A -169.87(12) . . . . ?
C1A C2A C3A C4A -173.94(15) . . . . ?
C1A N1A C5A C6A' 169.39(19) . . . . ?
C1A N1A C5A C6A -173.15(15) . . . . ?
C8A C7A C6A C5A 174.6(4) . . . . ?
N1A C5A C6A C7A 166.0(2) . . . . ?
C6A' C5A C6A C7A -46.4(5) . . . . ?
C1B N1B C5B C6B 173.15(11) . . . . ?
C5B N1B C1B C2B 176.29(11) . . . . ?
N1B C1B C2B C3B -177.06(11) . . . . ?
N1B C5B C6B C7B 179.22(11) . . . . ?
C5B C6B C7B C8B 175.48(13) . . . . ?
C1B C2B C3B C4B 170.28(14) . . . . ?
N1A C5A C6A' C7A' 82.0(4) . . . . ?
C6A C5A C6A' C7A' 41.5(4) . . . . ?
C8A' C7A' C6A' C5A 173.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.15
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 969503'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Di-n-butylammonium-1,1'-binaphthyl-2,2'-dicarboxylate  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H52 N2 O4'
_chemical_formula_weight         600.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.8142(13)
_cell_length_b                   12.3251(14)
_cell_length_c                   13.3363(15)
_cell_angle_alpha                64.614(2)
_cell_angle_beta                 86.613(2)
_cell_angle_gamma                83.622(2)
_cell_volume                     1743.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11330
_cell_measurement_theta_min      0.46
_cell_measurement_theta_max      27.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 'SADABS; Sheldrick, 1996' 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            11330
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.14
_reflns_number_total             7593
_reflns_number_gt                4937
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7593
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O 0.29745(10) 0.43392(11) 0.07006(10) 0.0328(3) Uani 1 1 d . . .
O2 O 0.30031(10) 0.05841(11) 0.41303(10) 0.0331(3) Uani 1 1 d . . .
O1 O 0.44508(10) 0.05834(11) 0.29702(10) 0.0357(3) Uani 1 1 d . . .
O2' O 0.41857(10) 0.41221(12) 0.20141(11) 0.0366(3) Uani 1 1 d . . .
C1' C 0.15953(13) 0.28214(14) 0.27270(13) 0.0225(3) Uani 1 1 d . . .
C1 C 0.17384(13) 0.21258(14) 0.20350(13) 0.0230(3) Uani 1 1 d . . .
C9 C 0.09987(13) 0.24572(14) 0.11127(14) 0.0254(4) Uani 1 1 d . . .
C9' C 0.07438(13) 0.25510(15) 0.35934(13) 0.0253(4) Uani 1 1 d . . .
N1A N 0.61744(13) 0.37918(14) 0.10633(13) 0.0313(3) Uani 1 1 d . . .
C11 C 0.34101(14) 0.07702(14) 0.31876(14) 0.0266(4) Uani 1 1 d . . .
C2 C 0.25974(13) 0.12011(15) 0.22287(14) 0.0249(4) Uani 1 1 d . . .
C10' C 0.06345(14) 0.31971(16) 0.42655(14) 0.0288(4) Uani 1 1 d . . .
C11' C 0.32228(14) 0.40736(14) 0.16813(15) 0.0259(4) Uani 1 1 d . . .
C3 C 0.27405(15) 0.06009(16) 0.15281(15) 0.0319(4) Uani 1 1 d . . .
H3 H 0.3342 -0.0023 0.1667 0.038 Uiso 1 1 calc R . .
C3' C 0.21657(14) 0.43595(15) 0.32287(15) 0.0294(4) Uani 1 1 d . . .
H3' H 0.2653 0.4970 0.3104 0.035 Uiso 1 1 calc R . .
C8' C 0.00030(14) 0.16424(16) 0.38208(15) 0.0326(4) Uani 1 1 d . . .
H8' H 0.0048 0.1214 0.3371 0.039 Uiso 1 1 calc R . .
C8 C 0.00986(14) 0.33965(15) 0.08610(15) 0.0291(4) Uani 1 1 d . . .
H8 H -0.0020 0.3822 0.1313 0.035 Uiso 1 1 calc R . .
C10 C 0.11477(14) 0.18393(16) 0.04241(14) 0.0294(4) Uani 1 1 d . . .
C7 C -0.06014(15) 0.37012(18) -0.00200(16) 0.0368(4) Uani 1 1 d . . .
H7 H -0.1199 0.4331 -0.0171 0.044 Uiso 1 1 calc R . .
C2' C 0.22928(13) 0.37170(14) 0.25636(14) 0.0243(4) Uani 1 1 d . . .
C4' C 0.13569(15) 0.41181(16) 0.40446(15) 0.0318(4) Uani 1 1 d . . .
H4' H 0.1276 0.4573 0.4471 0.038 Uiso 1 1 calc R . .
C1A C 0.69786(15) 0.36523(17) 0.19389(15) 0.0347(4) Uani 1 1 d . . .
H1A1 H 0.7753 0.3391 0.1751 0.042 Uiso 1 1 calc R . .
H1A2 H 0.6746 0.3017 0.2657 0.042 Uiso 1 1 calc R . .
C5 C 0.04135(16) 0.21803(18) -0.04850(16) 0.0387(5) Uani 1 1 d . . .
H5 H 0.0517 0.1771 -0.0951 0.046 Uiso 1 1 calc R . .
C4 C 0.20364(16) 0.08962(17) 0.06586(15) 0.0343(4) Uani 1 1 d . . .
H4 H 0.2141 0.0469 0.0208 0.041 Uiso 1 1 calc R . .
C7' C -0.07780(16) 0.13687(18) 0.46761(17) 0.0400(5) Uani 1 1 d . . .
H7' H -0.1273 0.0763 0.4807 0.048 Uiso 1 1 calc R . .
C5' C -0.01723(15) 0.28831(18) 0.51511(15) 0.0369(4) Uani 1 1 d . . .
H5' H -0.0243 0.3306 0.5606 0.044 Uiso 1 1 calc R . .
C2A C 0.70061(16) 0.48130(18) 0.20557(16) 0.0379(4) Uani 1 1 d . . .
H2A2 H 0.6249 0.5034 0.2311 0.046 Uiso 1 1 calc R . .
H2A1 H 0.7169 0.5466 0.1322 0.046 Uiso 1 1 calc R . .
C6' C -0.08471(16) 0.19806(19) 0.53571(17) 0.0417(5) Uani 1 1 d . . .
H6' H -0.1368 0.1765 0.5967 0.050 Uiso 1 1 calc R . .
C6 C -0.04417(17) 0.30909(19) -0.06999(16) 0.0423(5) Uani 1 1 d . . .
H6 H -0.0929 0.3310 -0.1312 0.051 Uiso 1 1 calc R . .
C6A C 0.53952(17) 0.28667(16) -0.00485(16) 0.0379(4) Uani 1 1 d . . .
H6A1 H 0.5612 0.3555 -0.0737 0.045 Uiso 1 1 calc R . .
H6A2 H 0.4605 0.3068 0.0153 0.045 Uiso 1 1 calc R . .
C5A C 0.61798(16) 0.26914(17) 0.08686(17) 0.0395(5) Uani 1 1 d . . .
H5A2 H 0.5947 0.2020 0.1562 0.047 Uiso 1 1 calc R . .
H5A1 H 0.6965 0.2462 0.0678 0.047 Uiso 1 1 calc R . .
C8A C 0.4633(2) 0.1893(2) -0.1158(2) 0.0564(6) Uani 1 1 d . . .
H8A3 H 0.3849 0.2050 -0.0934 0.085 Uiso 1 1 calc R . .
H8A2 H 0.4702 0.1150 -0.1266 0.085 Uiso 1 1 calc R . .
H8A1 H 0.4824 0.2569 -0.1853 0.085 Uiso 1 1 calc R . .
C7A C 0.5437(2) 0.17525(19) -0.0266(2) 0.0506(6) Uani 1 1 d . . .
H7A1 H 0.6224 0.1567 -0.0486 0.061 Uiso 1 1 calc R . .
H7A2 H 0.5246 0.1060 0.0431 0.061 Uiso 1 1 calc R . .
C3A C 0.78989(19) 0.4705(2) 0.28701(19) 0.0498(5) Uani 1 1 d . . .
H3A2 H 0.7763 0.4015 0.3588 0.060 Uiso 1 1 calc R . .
H3A1 H 0.8659 0.4530 0.2589 0.060 Uiso 1 1 calc R . .
C4A C 0.7902(2) 0.5824(2) 0.3061(2) 0.0654(7) Uani 1 1 d . . .
H4A1 H 0.8010 0.6517 0.2350 0.098 Uiso 1 1 calc R . .
H4A2 H 0.8523 0.5717 0.3559 0.098 Uiso 1 1 calc R . .
H4A3 H 0.7173 0.5967 0.3396 0.098 Uiso 1 1 calc R . .
N1B N 0.42196(13) 0.11713(14) 0.54118(13) 0.0289(3) Uani 1 1 d . . .
C5B C 0.33091(15) 0.15599(16) 0.60435(16) 0.0329(4) Uani 1 1 d . . .
H5B1 H 0.2841 0.2277 0.5522 0.039 Uiso 1 1 calc R . .
H5B2 H 0.3662 0.1790 0.6570 0.039 Uiso 1 1 calc R . .
C6B C 0.25567(17) 0.05643(18) 0.66746(17) 0.0414(5) Uani 1 1 d . . .
H6B1 H 0.2085 0.0453 0.6142 0.050 Uiso 1 1 calc R . .
H6B2 H 0.3041 -0.0199 0.7070 0.050 Uiso 1 1 calc R . .
C1B C 0.48562(17) 0.21609(18) 0.45746(16) 0.0409(5) Uani 1 1 d . . .
H1B1 H 0.4359 0.2633 0.3928 0.049 Uiso 1 1 calc R . .
H1B2 H 0.5528 0.1793 0.4312 0.049 Uiso 1 1 calc R . .
C7B C 0.17874(18) 0.0825(2) 0.75016(18) 0.0479(5) Uani 1 1 d . . .
H7B2 H 0.2263 0.0866 0.8068 0.058 Uiso 1 1 calc R . .
H7B1 H 0.1360 0.1626 0.7113 0.058 Uiso 1 1 calc R . .
C2B C 0.52588(19) 0.3019(2) 0.49896(19) 0.0518(6) Uani 1 1 d . . .
H2B1 H 0.5627 0.3663 0.4365 0.062 Uiso 1 1 calc R . .
H2B2 H 0.4586 0.3405 0.5232 0.062 Uiso 1 1 calc R . .
C8B C 0.0949(2) -0.0094(2) 0.8078(2) 0.0664(7) Uani 1 1 d . . .
H8B3 H 0.1359 -0.0900 0.8422 0.100 Uiso 1 1 calc R . .
H8B1 H 0.0411 -0.0070 0.7536 0.100 Uiso 1 1 calc R . .
H8B2 H 0.0533 0.0091 0.8652 0.100 Uiso 1 1 calc R . .
C3B C 0.60699(19) 0.2445(2) 0.5920(2) 0.0560(6) Uani 1 1 d . . .
H3B1 H 0.6710 0.1989 0.5710 0.067 Uiso 1 1 calc R . .
H3B2 H 0.5680 0.1865 0.6577 0.067 Uiso 1 1 calc R . .
C4B C 0.6544(2) 0.3377(3) 0.6224(3) 0.0741(8) Uani 1 1 d . . .
H4B3 H 0.5912 0.3849 0.6409 0.111 Uiso 1 1 calc R . .
H4B1 H 0.6978 0.3918 0.5593 0.111 Uiso 1 1 calc R . .
H4B2 H 0.7044 0.2958 0.6866 0.111 Uiso 1 1 calc R . .
H1' H 0.3827(18) 0.0842(19) 0.4971(18) 0.046(6) Uiso 1 1 d . . .
H2 H 0.5481(19) 0.3981(18) 0.1279(17) 0.041(6) Uiso 1 1 d . . .
H2' H 0.472(2) 0.058(2) 0.5906(19) 0.052(6) Uiso 1 1 d . . .
H1 H 0.6369(17) 0.4442(19) 0.0392(18) 0.039(5) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1' C11' 1.249(2) . ?
O2 C11 1.253(2) . ?
O1 C11 1.265(2) . ?
O2' C11' 1.262(2) . ?
C1' C2' 1.386(2) . ?
C1' C9' 1.437(2) . ?
C1' C1 1.498(2) . ?
C1 C2 1.385(2) . ?
C1 C9 1.435(2) . ?
C9 C10 1.416(2) . ?
C9 C8 1.421(2) . ?
C9' C8' 1.417(2) . ?
C9' C10' 1.425(2) . ?
N1A C5A 1.485(3) . ?
N1A C1A 1.489(2) . ?
N1A H2 0.89(2) . ?
N1A H1 0.95(2) . ?
C11 C2 1.513(2) . ?
C2 C3 1.412(2) . ?
C10' C4' 1.415(3) . ?
C10' C5' 1.418(2) . ?
C11' C2' 1.515(2) . ?
C3 C4 1.361(3) . ?
C3 H3 0.9500 . ?
C3' C4' 1.360(2) . ?
C3' C2' 1.413(2) . ?
C3' H3' 0.9500 . ?
C8' C7' 1.372(2) . ?
C8' H8' 0.9500 . ?
C8 C7 1.369(3) . ?
C8 H8 0.9500 . ?
C10 C5 1.416(2) . ?
C10 C4 1.417(2) . ?
C7 C6 1.399(3) . ?
C7 H7 0.9500 . ?
C4' H4' 0.9500 . ?
C1A C2A 1.508(3) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C7' C6' 1.402(3) . ?
C7' H7' 0.9500 . ?
C5' C6' 1.363(3) . ?
C5' H5' 0.9500 . ?
C2A C3A 1.513(3) . ?
C2A H2A2 0.9900 . ?
C2A H2A1 0.9900 . ?
C6' H6' 0.9500 . ?
C6 H6 0.9500 . ?
C6A C5A 1.505(3) . ?
C6A C7A 1.515(3) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C5A H5A2 0.9900 . ?
C5A H5A1 0.9900 . ?
C8A C7A 1.506(3) . ?
C8A H8A3 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A1 0.9800 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C3A C4A 1.507(3) . ?
C3A H3A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
N1B C5B 1.490(2) . ?
N1B C1B 1.496(2) . ?
N1B H1' 1.00(2) . ?
N1B H2' 0.93(2) . ?
C5B C6B 1.508(3) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B C7B 1.505(3) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C1B C2B 1.515(3) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C7B C8B 1.505(3) . ?
C7B H7B2 0.9900 . ?
C7B H7B1 0.9900 . ?
C2B C3B 1.481(3) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C8B H8B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C3B C4B 1.540(3) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B H4B3 0.9800 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' C1' C9' 118.67(15) . . ?
C2' C1' C1 120.96(14) . . ?
C9' C1' C1 120.35(14) . . ?
C2 C1 C9 118.69(15) . . ?
C2 C1 C1' 121.89(14) . . ?
C9 C1 C1' 119.36(14) . . ?
C10 C9 C8 117.85(15) . . ?
C10 C9 C1 120.18(15) . . ?
C8 C9 C1 121.97(16) . . ?
C8' C9' C10' 117.87(15) . . ?
C8' C9' C1' 122.23(16) . . ?
C10' C9' C1' 119.89(15) . . ?
C5A N1A C1A 113.47(14) . . ?
C5A N1A H2 110.0(13) . . ?
C1A N1A H2 106.9(13) . . ?
C5A N1A H1 109.1(12) . . ?
C1A N1A H1 108.6(12) . . ?
H2 N1A H1 108.7(18) . . ?
O2 C11 O1 125.37(16) . . ?
O2 C11 C2 118.17(15) . . ?
O1 C11 C2 116.40(15) . . ?
C1 C2 C3 120.41(15) . . ?
C1 C2 C11 122.85(15) . . ?
C3 C2 C11 116.74(15) . . ?
C4' C10' C5' 121.81(17) . . ?
C4' C10' C9' 118.82(16) . . ?
C5' C10' C9' 119.35(17) . . ?
O1' C11' O2' 125.80(15) . . ?
O1' C11' C2' 118.73(14) . . ?
O2' C11' C2' 115.39(15) . . ?
C4 C3 C2 121.50(16) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C4' C3' C2' 121.04(16) . . ?
C4' C3' H3' 119.5 . . ?
C2' C3' H3' 119.5 . . ?
C7' C8' C9' 121.38(18) . . ?
C7' C8' H8' 119.3 . . ?
C9' C8' H8' 119.3 . . ?
C7 C8 C9 121.32(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C9 C10 C5 119.48(16) . . ?
C9 C10 C4 119.02(16) . . ?
C5 C10 C4 121.50(17) . . ?
C8 C7 C6 120.37(18) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C1' C2' C3' 120.79(15) . . ?
C1' C2' C11' 123.30(15) . . ?
C3' C2' C11' 115.91(14) . . ?
C3' C4' C10' 120.75(16) . . ?
C3' C4' H4' 119.6 . . ?
C10' C4' H4' 119.6 . . ?
N1A C1A C2A 111.76(15) . . ?
N1A C1A H1A1 109.3 . . ?
C2A C1A H1A1 109.3 . . ?
N1A C1A H1A2 109.3 . . ?
C2A C1A H1A2 109.3 . . ?
H1A1 C1A H1A2 107.9 . . ?
C6 C5 C10 120.84(18) . . ?
C6 C5 H5 119.6 . . ?
C10 C5 H5 119.6 . . ?
C3 C4 C10 120.19(17) . . ?
C3 C4 H4 119.9 . . ?
C10 C4 H4 119.9 . . ?
C8' C7' C6' 120.13(18) . . ?
C8' C7' H7' 119.9 . . ?
C6' C7' H7' 119.9 . . ?
C6' C5' C10' 120.71(18) . . ?
C6' C5' H5' 119.6 . . ?
C10' C5' H5' 119.6 . . ?
C1A C2A C3A 111.84(16) . . ?
C1A C2A H2A2 109.2 . . ?
C3A C2A H2A2 109.2 . . ?
C1A C2A H2A1 109.2 . . ?
C3A C2A H2A1 109.2 . . ?
H2A2 C2A H2A1 107.9 . . ?
C5' C6' C7' 120.49(17) . . ?
C5' C6' H6' 119.8 . . ?
C7' C6' H6' 119.8 . . ?
C5 C6 C7 120.13(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C5A C6A C7A 112.13(16) . . ?
C5A C6A H6A1 109.2 . . ?
C7A C6A H6A1 109.2 . . ?
C5A C6A H6A2 109.2 . . ?
C7A C6A H6A2 109.2 . . ?
H6A1 C6A H6A2 107.9 . . ?
N1A C5A C6A 112.60(15) . . ?
N1A C5A H5A2 109.1 . . ?
C6A C5A H5A2 109.1 . . ?
N1A C5A H5A1 109.1 . . ?
C6A C5A H5A1 109.1 . . ?
H5A2 C5A H5A1 107.8 . . ?
C7A C8A H8A3 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A3 C8A H8A2 109.5 . . ?
C7A C8A H8A1 109.5 . . ?
H8A3 C8A H8A1 109.5 . . ?
H8A2 C8A H8A1 109.5 . . ?
C8A C7A C6A 113.15(18) . . ?
C8A C7A H7A1 108.9 . . ?
C6A C7A H7A1 108.9 . . ?
C8A C7A H7A2 108.9 . . ?
C6A C7A H7A2 108.9 . . ?
H7A1 C7A H7A2 107.8 . . ?
C4A C3A C2A 113.27(19) . . ?
C4A C3A H3A2 108.9 . . ?
C2A C3A H3A2 108.9 . . ?
C4A C3A H3A1 108.9 . . ?
C2A C3A H3A1 108.9 . . ?
H3A2 C3A H3A1 107.7 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C5B N1B C1B 115.28(15) . . ?
C5B N1B H1' 106.3(12) . . ?
C1B N1B H1' 105.2(12) . . ?
C5B N1B H2' 109.4(14) . . ?
C1B N1B H2' 109.9(14) . . ?
H1' N1B H2' 110.6(18) . . ?
N1B C5B C6B 111.11(15) . . ?
N1B C5B H5B1 109.4 . . ?
C6B C5B H5B1 109.4 . . ?
N1B C5B H5B2 109.4 . . ?
C6B C5B H5B2 109.4 . . ?
H5B1 C5B H5B2 108.0 . . ?
C7B C6B C5B 112.46(17) . . ?
C7B C6B H6B1 109.1 . . ?
C5B C6B H6B1 109.1 . . ?
C7B C6B H6B2 109.1 . . ?
C5B C6B H6B2 109.1 . . ?
H6B1 C6B H6B2 107.8 . . ?
N1B C1B C2B 115.03(16) . . ?
N1B C1B H1B1 108.5 . . ?
C2B C1B H1B1 108.5 . . ?
N1B C1B H1B2 108.5 . . ?
C2B C1B H1B2 108.5 . . ?
H1B1 C1B H1B2 107.5 . . ?
C8B C7B C6B 114.19(19) . . ?
C8B C7B H7B2 108.7 . . ?
C6B C7B H7B2 108.7 . . ?
C8B C7B H7B1 108.7 . . ?
C6B C7B H7B1 108.7 . . ?
H7B2 C7B H7B1 107.6 . . ?
C3B C2B C1B 114.46(19) . . ?
C3B C2B H2B1 108.6 . . ?
C1B C2B H2B1 108.6 . . ?
C3B C2B H2B2 108.6 . . ?
C1B C2B H2B2 108.6 . . ?
H2B1 C2B H2B2 107.6 . . ?
C7B C8B H8B3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
H8B3 C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C2B C3B C4B 112.1(2) . . ?
C2B C3B H3B1 109.2 . . ?
C4B C3B H3B1 109.2 . . ?
C2B C3B H3B2 109.2 . . ?
C4B C3B H3B2 109.2 . . ?
H3B1 C3B H3B2 107.9 . . ?
C3B C4B H4B3 109.5 . . ?
C3B C4B H4B1 109.5 . . ?
H4B3 C4B H4B1 109.5 . . ?
C3B C4B H4B2 109.5 . . ?
H4B3 C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2' C1' C1 C2 78.0(2) . . . . ?
C9' C1' C1 C2 -100.64(18) . . . . ?
C2' C1' C1 C9 -99.23(18) . . . . ?
C9' C1' C1 C9 82.18(19) . . . . ?
C2 C1 C9 C10 0.4(2) . . . . ?
C1' C1 C9 C10 177.67(14) . . . . ?
C2 C1 C9 C8 -179.99(15) . . . . ?
C1' C1 C9 C8 -2.7(2) . . . . ?
C2' C1' C9' C8' -179.47(15) . . . . ?
C1 C1' C9' C8' -0.8(2) . . . . ?
C2' C1' C9' C10' -0.2(2) . . . . ?
C1 C1' C9' C10' 178.38(14) . . . . ?
C9 C1 C2 C3 0.2(2) . . . . ?
C1' C1 C2 C3 -177.05(15) . . . . ?
C9 C1 C2 C11 -179.02(14) . . . . ?
C1' C1 C2 C11 3.8(2) . . . . ?
O2 C11 C2 C1 46.6(2) . . . . ?
O1 C11 C2 C1 -136.01(17) . . . . ?
O2 C11 C2 C3 -132.59(17) . . . . ?
O1 C11 C2 C3 44.8(2) . . . . ?
C8' C9' C10' C4' -179.27(16) . . . . ?
C1' C9' C10' C4' 1.5(2) . . . . ?
C8' C9' C10' C5' 2.2(2) . . . . ?
C1' C9' C10' C5' -177.03(15) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C11 C2 C3 C4 178.26(16) . . . . ?
C10' C9' C8' C7' -1.5(3) . . . . ?
C1' C9' C8' C7' 177.71(16) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C1 C9 C8 C7 -179.88(16) . . . . ?
C8 C9 C10 C5 0.6(2) . . . . ?
C1 C9 C10 C5 -179.76(15) . . . . ?
C8 C9 C10 C4 -179.80(15) . . . . ?
C1 C9 C10 C4 -0.2(2) . . . . ?
C9 C8 C7 C6 -0.2(3) . . . . ?
C9' C1' C2' C3' -0.5(2) . . . . ?
C1 C1' C2' C3' -179.09(15) . . . . ?
C9' C1' C2' C11' 179.63(14) . . . . ?
C1 C1' C2' C11' 1.0(2) . . . . ?
C4' C3' C2' C1' -0.1(2) . . . . ?
C4' C3' C2' C11' 179.84(15) . . . . ?
O1' C11' C2' C1' 52.8(2) . . . . ?
O2' C11' C2' C1' -130.17(17) . . . . ?
O1' C11' C2' C3' -127.14(17) . . . . ?
O2' C11' C2' C3' 49.9(2) . . . . ?
C2' C3' C4' C10' 1.3(3) . . . . ?
C5' C10' C4' C3' 176.43(16) . . . . ?
C9' C10' C4' C3' -2.0(3) . . . . ?
C5A N1A C1A C2A 176.09(15) . . . . ?
C9 C10 C5 C6 -0.5(3) . . . . ?
C4 C10 C5 C6 179.89(18) . . . . ?
C2 C3 C4 C10 1.2(3) . . . . ?
C9 C10 C4 C3 -0.6(3) . . . . ?
C5 C10 C4 C3 178.96(17) . . . . ?
C9' C8' C7' C6' -0.8(3) . . . . ?
C4' C10' C5' C6' -179.04(17) . . . . ?
C9' C10' C5' C6' -0.6(3) . . . . ?
N1A C1A C2A C3A -174.85(16) . . . . ?
C10' C5' C6' C7' -1.8(3) . . . . ?
C8' C7' C6' C5' 2.6(3) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
C8 C7 C6 C5 0.3(3) . . . . ?
C1A N1A C5A C6A -177.80(15) . . . . ?
C7A C6A C5A N1A 178.08(16) . . . . ?
C5A C6A C7A C8A 178.29(18) . . . . ?
C1A C2A C3A C4A -176.47(18) . . . . ?
C1B N1B C5B C6B 167.61(16) . . . . ?
N1B C5B C6B C7B 168.10(17) . . . . ?
C5B N1B C1B C2B 47.4(2) . . . . ?
C5B C6B C7B C8B 174.9(2) . . . . ?
N1B C1B C2B C3B 61.7(2) . . . . ?
C1B C2B C3B C4B 174.04(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.14
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 969504'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C53 H81 N5 O7'
_chemical_formula_weight         900.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.254(3)
_cell_length_b                   14.900(3)
_cell_length_c                   15.067(3)
_cell_angle_alpha                100.82(3)
_cell_angle_beta                 117.76(3)
_cell_angle_gamma                104.12(3)
_cell_volume                     2571.3(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10474
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 none 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ scans and ω scans'
_diffrn_reflns_number            10477
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         26.39
_reflns_number_total             10477
_reflns_number_gt                8075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1047P)²+1.0472P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10477
_refine_ls_number_parameters     698
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1829
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50362(12) 0.13120(9) 0.55780(10) 0.0353(3) Uani 1 1 d . . .
O4 O 0.25755(12) 0.02503(10) 0.20597(11) 0.0420(3) Uani 1 1 d . . .
O3 O 0.10909(12) 0.07026(10) 0.14085(11) 0.0398(3) Uani 1 1 d . . .
O2 O 0.50323(14) 0.25405(10) 0.49609(11) 0.0472(4) Uani 1 1 d . . .
C1' C 0.76250(14) 0.38401(12) 0.70142(13) 0.0252(3) Uani 1 1 d . . .
N1D N 0.09962(15) -0.06865(12) 0.04081(13) 0.0392(4) Uani 1 1 d . . .
C2 C 0.57794(14) 0.28984(12) 0.68329(13) 0.0261(4) Uani 1 1 d . . .
C2' C 0.78660(14) 0.46577(12) 0.67339(13) 0.0273(4) Uani 1 1 d . B .
C11' C 0.72642(15) 0.53726(12) 0.66984(14) 0.0286(4) Uani 1 1 d . . .
C1 C 0.68448(14) 0.36567(12) 0.74222(13) 0.0249(3) Uani 1 1 d . . .
O5 O 0.39149(14) 0.21055(12) 0.22607(13) 0.0556(4) Uani 1 1 d D . .
C11 C 0.52637(14) 0.22157(12) 0.57019(14) 0.0269(4) Uani 1 1 d . . .
C8 C 0.84054(16) 0.49824(13) 0.91846(15) 0.0334(4) Uani 1 1 d . . .
H8 H 0.8867 0.5145 0.8899 0.040 Uiso 1 1 calc R . .
C9' C 0.82153(14) 0.31888(12) 0.70153(13) 0.0280(4) Uani 1 1 d . . .
C9 C 0.72921(15) 0.42239(12) 0.85134(14) 0.0278(4) Uani 1 1 d . . .
C10' C 0.90117(15) 0.33731(14) 0.66869(15) 0.0340(4) Uani 1 1 d . . .
C22 C 0.15813(16) 0.01102(13) 0.13217(15) 0.0336(4) Uani 1 1 d . . .
C3 C 0.51266(16) 0.26914(13) 0.72994(15) 0.0331(4) Uani 1 1 d . . .
H3 H 0.4395 0.2166 0.6887 0.040 Uiso 1 1 calc R . .
C10 C 0.66207(17) 0.40029(13) 0.89651(15) 0.0329(4) Uani 1 1 d . . .
C3' C 0.87068(16) 0.48545(14) 0.64657(15) 0.0340(4) Uani 1 1 d . . .
H3' H 0.8898 0.5438 0.6312 0.041 Uiso 1 1 calc R B .
C8' C 0.80460(16) 0.23577(13) 0.73426(15) 0.0348(4) Uani 1 1 d . . .
H8' H 0.7538 0.2234 0.7587 0.042 Uiso 1 1 calc R . .
C6 C 0.8163(2) 0.52572(15) 1.06770(16) 0.0439(5) Uani 1 1 d . . .
H6 H 0.8464 0.5602 1.1409 0.053 Uiso 1 1 calc R . .
C1D C 0.14760(17) -0.13835(14) 0.01611(15) 0.0357(4) Uani 1 1 d . . .
H29 H 0.2051 -0.1414 0.0853 0.043 Uiso 1 1 calc R . .
C7 C 0.88279(18) 0.54851(14) 1.02398(16) 0.0402(5) Uani 1 1 d . . .
H7 H 0.9575 0.5990 1.0674 0.048 Uiso 1 1 calc R . .
C4' C 0.92467(17) 0.42223(15) 0.64241(16) 0.0377(4) Uani 1 1 d . B .
H4' H 0.9786 0.4357 0.6216 0.045 Uiso 1 1 calc R . .
C4 C 0.55261(17) 0.32289(15) 0.83235(16) 0.0380(4) Uani 1 1 d . . .
H4 H 0.5065 0.3083 0.8613 0.046 Uiso 1 1 calc R . .
C7' C 0.86028(19) 0.17352(15) 0.73109(18) 0.0453(5) Uani 1 1 d . . .
H7' H 0.8478 0.1185 0.7532 0.054 Uiso 1 1 calc R . .
C5' C 0.95652(18) 0.27047(16) 0.66585(18) 0.0452(5) Uani 1 1 d . . .
H5' H 1.0089 0.2816 0.6431 0.054 Uiso 1 1 calc R . .
C5 C 0.7084(2) 0.45417(15) 1.00565(16) 0.0426(5) Uani 1 1 d . . .
H5 H 0.6636 0.4402 1.0359 0.051 Uiso 1 1 calc R . .
C6' C 0.9353(2) 0.19038(17) 0.6955(2) 0.0515(6) Uani 1 1 d . . .
H6' H 0.9720 0.1457 0.6919 0.062 Uiso 1 1 calc R . .
N1A N 0.21758(19) 0.25423(16) 0.08498(18) 0.0573(5) Uani 1 1 d D . .
C5D C 0.0992(2) -0.31661(15) -0.07991(19) 0.0468(5) Uani 1 1 d . . .
H5D1 H 0.1525 -0.3257 -0.0140 0.056 Uiso 1 1 calc R . .
H5D2 H 0.0344 -0.3809 -0.1281 0.056 Uiso 1 1 calc R . .
C2D C 0.20881(19) -0.10772(15) -0.03988(18) 0.0431(5) Uani 1 1 d . . .
H43A H 0.2725 -0.0426 0.0068 0.052 Uiso 1 1 calc R . .
H43B H 0.1545 -0.1009 -0.1070 0.052 Uiso 1 1 calc R . .
C1A C 0.20936(19) 0.23810(17) -0.01857(18) 0.0467(5) Uani 1 1 d . . .
H46 H 0.1429 0.2518 -0.0692 0.056 Uiso 1 1 calc R . .
C6D C 0.05375(18) -0.24100(14) -0.05095(18) 0.0417(5) Uani 1 1 d . . .
H6D2 H -0.0074 -0.2387 -0.1175 0.050 Uiso 1 1 calc R . .
H6D1 H 0.0195 -0.2619 -0.0105 0.050 Uiso 1 1 calc R . .
C4D C 0.1612(2) -0.28556(17) -0.1345(2) 0.0513(6) Uani 1 1 d . . .
H49A H 0.1060 -0.2847 -0.2051 0.062 Uiso 1 1 calc R . .
H49B H 0.1946 -0.3340 -0.1467 0.062 Uiso 1 1 calc R . .
C3D C 0.2563(2) -0.18313(17) -0.0658(2) 0.0501(5) Uani 1 1 d . . .
H50A H 0.3156 -0.1858 0.0016 0.060 Uiso 1 1 calc R . .
H50B H 0.2928 -0.1623 -0.1046 0.060 Uiso 1 1 calc R . .
C2A C 0.3191(2) 0.30782(18) 0.0013(2) 0.0559(6) Uani 1 1 d . . .
H54A H 0.3851 0.2963 0.0541 0.067 Uiso 1 1 calc R . .
H54B H 0.3289 0.3769 0.0312 0.067 Uiso 1 1 calc R . .
C6A C 0.1922(2) 0.13235(18) -0.0639(2) 0.0588(6) Uani 1 1 d . . .
H58A H 0.1172 0.0882 -0.0810 0.071 Uiso 1 1 calc R . .
H58B H 0.2529 0.1168 -0.0096 0.071 Uiso 1 1 calc R . .
C5A C 0.1962(3) 0.1135(2) -0.1647(2) 0.0784(9) Uani 1 1 d . . .
H60A H 0.1920 0.0453 -0.1885 0.094 Uiso 1 1 calc R . .
H60B H 0.1286 0.1193 -0.2225 0.094 Uiso 1 1 calc R . .
C3A C 0.3160(4) 0.2918(3) -0.1025(3) 0.0864(10) Uani 1 1 d . . .
H63A H 0.3872 0.3391 -0.0895 0.104 Uiso 1 1 calc R . .
H63B H 0.2501 0.3034 -0.1554 0.104 Uiso 1 1 calc R . .
C4A C 0.3047(3) 0.1857(2) -0.1464(3) 0.0816(9) Uani 1 1 d . . .
H65A H 0.3016 0.1746 -0.2148 0.098 Uiso 1 1 calc R . .
H65B H 0.3723 0.1751 -0.0949 0.098 Uiso 1 1 calc R . .
N1C N 0.25113(16) 0.21155(12) 0.33918(14) 0.0321(3) Uani 1 1 d . . .
C1C C 0.20947(17) 0.20204(14) 0.41198(16) 0.0358(4) Uani 1 1 d . . .
H35 H 0.2653 0.2573 0.4822 0.043 Uiso 1 1 calc R . .
C6C C 0.20301(19) 0.10522(16) 0.43156(19) 0.0446(5) Uani 1 1 d . . .
H41A H 0.2798 0.1016 0.4631 0.054 Uiso 1 1 calc R . .
H41B H 0.1499 0.0494 0.3626 0.054 Uiso 1 1 calc R . .
C2C C 0.09382(19) 0.21107(17) 0.3666(2) 0.0481(5) Uani 1 1 d . . .
H45A H 0.0375 0.1577 0.2962 0.058 Uiso 1 1 calc R . .
H45B H 0.1002 0.2752 0.3556 0.058 Uiso 1 1 calc R . .
C3C C 0.0519(2) 0.2040(2) 0.4427(2) 0.0587(6) Uani 1 1 d . . .
H51A H 0.1044 0.2610 0.5107 0.070 Uiso 1 1 calc R . .
H55B H -0.0253 0.2068 0.4103 0.070 Uiso 1 1 calc R . .
C4C C 0.0467(2) 0.1083(2) 0.4657(2) 0.0594(6) Uani 1 1 d . . .
H55A H 0.0253 0.1079 0.5195 0.071 Uiso 1 1 calc R . .
H4D2 H -0.0132 0.0516 0.3993 0.071 Uiso 1 1 calc R . .
C5C C 0.1611(2) 0.0967(2) 0.5074(2) 0.0616(7) Uani 1 1 d . . .
H56A H 0.1530 0.0315 0.5159 0.074 Uiso 1 1 calc R . .
H56B H 0.2187 0.1484 0.5787 0.074 Uiso 1 1 calc R . .
N1B N 0.45055(15) 0.01744(13) 0.36192(14) 0.0303(3) Uani 1 1 d . . .
C1B C 0.53295(16) 0.06396(14) 0.33345(15) 0.0327(4) Uani 1 1 d . . .
H26 H 0.5258 0.1277 0.3260 0.039 Uiso 1 1 calc R . .
C6B C 0.65539(17) 0.08702(17) 0.42200(16) 0.0413(5) Uani 1 1 d . . .
H40A H 0.6635 0.0255 0.4338 0.050 Uiso 1 1 calc R . .
H40B H 0.6736 0.1332 0.4896 0.050 Uiso 1 1 calc R . .
C2B C 0.50265(19) -0.00190(18) 0.22754(17) 0.0479(5) Uani 1 1 d . . .
H42A H 0.4234 -0.0134 0.1716 0.057 Uiso 1 1 calc R . .
H42B H 0.5058 -0.0666 0.2321 0.057 Uiso 1 1 calc R . .
C5B C 0.73856(19) 0.13344(19) 0.39128(19) 0.0507(5) Uani 1 1 d . . .
H44A H 0.7369 0.1989 0.3884 0.061 Uiso 1 1 calc R . .
H44B H 0.8174 0.1436 0.4470 0.061 Uiso 1 1 calc R . .
C4B C 0.7087(2) 0.0693(2) 0.2837(2) 0.0578(6) Uani 1 1 d . . .
H52A H 0.7609 0.1041 0.2643 0.069 Uiso 1 1 calc R . .
H52B H 0.7200 0.0071 0.2891 0.069 Uiso 1 1 calc R . .
C3B C 0.5857(2) 0.0452(2) 0.1966(2) 0.0618(7) Uani 1 1 d . . .
H57A H 0.5671 -0.0009 0.1288 0.074 Uiso 1 1 calc R . .
H57B H 0.5767 0.1065 0.1848 0.074 Uiso 1 1 calc R . .
C6E C 0.6718(5) 0.3859(5) 0.3727(4) 0.0418(11) Uani 0.805(7) 1 d P A 1
H53A H 0.6176 0.3251 0.3090 0.050 Uiso 0.805(7) 1 calc PR A 1
H6E1 H 0.7054 0.3661 0.4362 0.050 Uiso 0.805(7) 1 calc PR A 1
C2E C 0.5594(3) 0.4866(3) 0.2940(3) 0.0499(9) Uani 0.805(7) 1 d P A 1
H59A H 0.4984 0.4305 0.2273 0.060 Uiso 0.805(7) 1 calc PR A 1
H59B H 0.5250 0.5330 0.3091 0.060 Uiso 0.805(7) 1 calc PR A 1
C4E C 0.7180(6) 0.4762(7) 0.2653(5) 0.078(2) Uani 0.805(7) 1 d P A 1
H61A H 0.7814 0.5155 0.2606 0.094 Uiso 0.805(7) 1 calc PR A 1
H61B H 0.6657 0.4185 0.1979 0.094 Uiso 0.805(7) 1 calc PR A 1
C3E C 0.6537(9) 0.5387(6) 0.2792(9) 0.079(3) Uani 0.805(7) 1 d P A 1
H62A H 0.6196 0.5582 0.2155 0.095 Uiso 0.805(7) 1 calc PR A 1
H62B H 0.7085 0.5999 0.3423 0.095 Uiso 0.805(7) 1 calc PR A 1
C5E C 0.7664(3) 0.4409(3) 0.3598(4) 0.0630(11) Uani 0.805(7) 1 d P A 1
H64A H 0.8046 0.3968 0.3480 0.076 Uiso 0.805(7) 1 calc PR A 1
H64B H 0.8244 0.4984 0.4261 0.076 Uiso 0.805(7) 1 calc PR A 1
C1E C 0.6076(3) 0.4489(2) 0.3859(3) 0.0323(7) Uani 0.805(7) 1 d P A 1
H1E H 0.6616 0.5069 0.4540 0.039 Uiso 0.805(7) 1 calc PR A 1
C2F C 0.6136(13) 0.5360(11) 0.3615(15) 0.047(4) Uani 0.195(7) 1 d P A 2
H2D1 H 0.6731 0.5615 0.4389 0.056 Uiso 0.195(7) 1 calc PR A 2
H2D2 H 0.5542 0.5634 0.3514 0.056 Uiso 0.195(7) 1 calc PR A 2
C4F C 0.753(2) 0.5160(19) 0.3100(19) 0.062(6) Uani 0.195(7) 1 d P A 2
H4F2 H 0.7814 0.5299 0.2636 0.074 Uiso 0.195(7) 1 calc PR A 2
H4F1 H 0.8194 0.5464 0.3849 0.074 Uiso 0.195(7) 1 calc PR A 2
C3F C 0.669(3) 0.570(2) 0.299(3) 0.048(5) Uani 0.195(7) 1 d P A 2
H3D1 H 0.7108 0.6426 0.3298 0.058 Uiso 0.195(7) 1 calc PR A 2
H3D2 H 0.6087 0.5518 0.2225 0.058 Uiso 0.195(7) 1 calc PR A 2
C5F C 0.7097(17) 0.4092(15) 0.2843(19) 0.070(5) Uani 0.195(7) 1 d P A 2
H5E2 H 0.7756 0.3883 0.3090 0.084 Uiso 0.195(7) 1 calc PR A 2
H5E1 H 0.6598 0.3767 0.2055 0.084 Uiso 0.195(7) 1 calc PR A 2
C6F C 0.6433(18) 0.3730(16) 0.3328(13) 0.034(4) Uani 0.195(7) 1 d P A 2
H6E2 H 0.6974 0.3865 0.4096 0.041 Uiso 0.195(7) 1 calc PR A 2
H18 H 0.6007 0.3007 0.2968 0.041 Uiso 0.195(7) 1 calc PR A 2
O1' O 0.61948(15) 0.49996(12) 0.61973(18) 0.0536(4) Uani 0.913(3) 1 d P B 3
O2' O 0.78673(16) 0.62614(12) 0.7113(2) 0.0536(4) Uani 0.913(3) 1 d P B 3
H21 H 0.030(2) -0.0704(18) -0.014(2) 0.053(7) Uiso 1 1 d . . .
H12 H 0.385(2) 0.0052(16) 0.313(2) 0.037(6) Uiso 1 1 d . . .
H15 H 0.2472(18) 0.2671(17) 0.3223(17) 0.034(5) Uiso 1 1 d . . .
H14 H 0.4525(19) -0.0365(19) 0.3661(18) 0.039(6) Uiso 1 1 d . . .
H17 H 0.201(2) 0.163(2) 0.273(2) 0.052(7) Uiso 1 1 d . . .
H13 H 0.4677(19) 0.0596(17) 0.426(2) 0.039(6) Uiso 1 1 d . . .
H16 H 0.326(2) 0.2168(19) 0.372(2) 0.055(7) Uiso 1 1 d . . .
C1F C 0.5594(11) 0.4232(9) 0.3217(13) 0.034(3) Uani 0.195(7) 1 d P A 2
H1D H 0.4919 0.3964 0.2463 0.041 Uiso 0.195(7) 1 calc PR A 2
N1E N 0.5085(5) 0.3927(3) 0.3913(5) 0.0271(9) Uani 0.805(7) 1 d P A 1
H9A H 0.4683 0.3323 0.3383 0.041 Uiso 0.805(7) 1 calc PR A 1
H10A H 0.4619 0.4269 0.3829 0.041 Uiso 0.805(7) 1 calc PR A 1
H11A H 0.5355 0.3849 0.4561 0.041 Uiso 0.805(7) 1 calc PR A 1
N9A N 0.526(3) 0.387(2) 0.394(3) 0.056(8) Uani 0.195(7) 1 d P A 2
H11 H 0.5879 0.4150 0.4628 0.083 Uiso 0.195(7) 1 calc PR A 2
H9 H 0.5041 0.3200 0.3733 0.083 Uiso 0.195(7) 1 calc PR A 2
H10 H 0.4677 0.4038 0.3897 0.083 Uiso 0.195(7) 1 calc PR A 2
O1A O 0.6594(16) 0.5298(13) 0.700(2) 0.0536(4) Uani 0.087(3) 1 d P B 4
O2A O 0.7483(17) 0.6053(13) 0.641(2) 0.0536(4) Uani 0.087(3) 1 d P B 4
H20 H 0.220(3) 0.3170(10) 0.108(3) 0.102(12) Uiso 1 1 d D . .
H1 H 0.3457(13) 0.2336(14) 0.1865(17) 0.059(5) Uiso 1 1 d D . .
H2 H 0.3623(15) 0.1525(8) 0.2238(19) 0.059(5) Uiso 1 1 d D . .
H19 H 0.153(2) 0.211(3) 0.076(4) 0.131(16) Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.261(2) . ?
O4 C22 1.260(2) . ?
O3 C22 1.276(2) . ?
O2 C11 1.236(2) . ?
C1' C2' 1.380(2) . ?
C1' C9' 1.431(2) . ?
C1' C1 1.497(2) . ?
N1D C22 1.354(3) . ?
N1D C1D 1.457(2) . ?
N1D H21 0.94(3) . ?
C2 C1 1.379(3) . ?
C2 C3 1.416(3) . ?
C2 C11 1.515(3) . ?
C2' C3' 1.418(3) . ?
C2' C11' 1.516(2) . ?
C11' O2A 1.21(2) . ?
C11' O1A 1.23(2) . ?
C11' O2' 1.232(2) . ?
C11' O1' 1.249(3) . ?
C1 C9 1.436(3) . ?
O5 H1 0.8500(4) . ?
O5 H2 0.8500(3) . ?
C8 C7 1.376(3) . ?
C8 C9 1.421(3) . ?
C8 H8 0.9500 . ?
C9' C8' 1.425(3) . ?
C9' C10' 1.425(3) . ?
C9 C10 1.423(3) . ?
C10' C4' 1.405(3) . ?
C10' C5' 1.420(3) . ?
C3 C4 1.357(3) . ?
C3 H3 0.9500 . ?
C10 C4 1.413(3) . ?
C10 C5 1.421(3) . ?
C3' C4' 1.364(3) . ?
C3' H3' 0.9500 . ?
C8' C7' 1.368(3) . ?
C8' H8' 0.9500 . ?
C6 C5 1.364(3) . ?
C6 C7 1.399(3) . ?
C6 H6 0.9500 . ?
C1D C6D 1.521(3) . ?
C1D C2D 1.522(3) . ?
C1D H29 1.0000 . ?
C7 H7 0.9500 . ?
C4' H4' 0.9500 . ?
C4 H4 0.9500 . ?
C7' C6' 1.396(3) . ?
C7' H7' 0.9500 . ?
C5' C6' 1.366(3) . ?
C5' H5' 0.9500 . ?
C5 H5 0.9500 . ?
C6' H6' 0.9500 . ?
N1A C1A 1.477(3) . ?
N1A H20 0.9200(3) . ?
N1A H19 0.9200(4) . ?
C5D C4D 1.514(3) . ?
C5D C6D 1.522(3) . ?
C5D H5D1 0.9900 . ?
C5D H5D2 0.9900 . ?
C2D C3D 1.525(3) . ?
C2D H43A 0.9900 . ?
C2D H43B 0.9900 . ?
C1A C6A 1.504(3) . ?
C1A C2A 1.506(3) . ?
C1A H46 1.0000 . ?
C6D H6D2 0.9900 . ?
C6D H6D1 0.9900 . ?
C4D C3D 1.526(4) . ?
C4D H49A 0.9900 . ?
C4D H49B 0.9900 . ?
C3D H50A 0.9900 . ?
C3D H50B 0.9900 . ?
C2A C3A 1.514(4) . ?
C2A H54A 0.9900 . ?
C2A H54B 0.9900 . ?
C6A C5A 1.522(4) . ?
C6A H58A 0.9900 . ?
C6A H58B 0.9900 . ?
C5A C4A 1.519(5) . ?
C5A H60A 0.9900 . ?
C5A H60B 0.9900 . ?
C3A C4A 1.531(4) . ?
C3A H63A 0.9900 . ?
C3A H63B 0.9900 . ?
C4A H65A 0.9900 . ?
C4A H65B 0.9900 . ?
N1C C1C 1.483(2) . ?
N1C H15 0.92(2) . ?
N1C H17 0.91(3) . ?
N1C H16 0.92(3) . ?
C1C C2C 1.515(3) . ?
C1C C6C 1.516(3) . ?
C1C H35 1.0000 . ?
C6C C5C 1.527(3) . ?
C6C H41A 0.9900 . ?
C6C H41B 0.9900 . ?
C2C C3C 1.529(3) . ?
C2C H45A 0.9900 . ?
C2C H45B 0.9900 . ?
C3C C4C 1.522(4) . ?
C3C H51A 0.9900 . ?
C3C H55B 0.9900 . ?
C4C C5C 1.519(4) . ?
C4C H55A 0.9900 . ?
C4C H4D2 0.9900 . ?
C5C H56A 0.9900 . ?
C5C H56B 0.9900 . ?
N1B C1B 1.493(2) . ?
N1B H12 0.82(3) . ?
N1B H14 0.82(3) . ?
N1B H13 0.93(2) . ?
C1B C2B 1.503(3) . ?
C1B C6B 1.520(3) . ?
C1B H26 1.0000 . ?
C6B C5B 1.526(3) . ?
C6B H40A 0.9900 . ?
C6B H40B 0.9900 . ?
C2B C3B 1.530(3) . ?
C2B H42A 0.9900 . ?
C2B H42B 0.9900 . ?
C5B C4B 1.517(4) . ?
C5B H44A 0.9900 . ?
C5B H44B 0.9900 . ?
C4B C3B 1.515(4) . ?
C4B H52A 0.9900 . ?
C4B H52B 0.9900 . ?
C3B H57A 0.9900 . ?
C3B H57B 0.9900 . ?
C6E C1E 1.509(7) . ?
C6E C5E 1.514(7) . ?
C6E H53A 0.9900 . ?
C6E H6E1 0.9900 . ?
C2E C3E 1.515(9) . ?
C2E C1E 1.516(5) . ?
C2E H59A 0.9900 . ?
C2E H59B 0.9900 . ?
C4E C3E 1.508(12) . ?
C4E C5E 1.524(9) . ?
C4E H61A 0.9900 . ?
C4E H61B 0.9900 . ?
C3E H62A 0.9900 . ?
C3E H62B 0.9900 . ?
C5E H64A 0.9900 . ?
C5E H64B 0.9900 . ?
C1E N1E 1.502(5) . ?
C1E H1E 1.0000 . ?
C2F C1F 1.529(19) . ?
C2F C3F 1.56(3) . ?
C2F H2D1 0.9900 . ?
C2F H2D2 0.9900 . ?
C4F C5F 1.46(3) . ?
C4F C3F 1.56(4) . ?
C4F H4F2 0.9900 . ?
C4F H4F1 0.9900 . ?
C3F H3D1 0.9900 . ?
C3F H3D2 0.9900 . ?
C5F C6F 1.50(3) . ?
C5F H5E2 0.9900 . ?
C5F H5E1 0.9900 . ?
C6F C1F 1.52(3) . ?
C6F H6E2 0.9900 . ?
C6F H18 0.9900 . ?
C1F N9A 1.51(3) . ?
C1F H1D 1.0000 . ?
N1E H9A 0.9100 . ?
N1E H10A 0.9100 . ?
N1E H11A 0.9100 . ?
N9A H11 0.9100 . ?
N9A H9 0.9100 . ?
N9A H10 0.9100 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' C1' C9' 119.57(16) . . ?
C2' C1' C1 122.20(15) . . ?
C9' C1' C1 117.97(14) . . ?
C22 N1D C1D 124.03(16) . . ?
C22 N1D H21 115.8(15) . . ?
C1D N1D H21 119.0(15) . . ?
C1 C2 C3 120.01(16) . . ?
C1 C2 C11 123.68(16) . . ?
C3 C2 C11 116.23(15) . . ?
C1' C2' C3' 119.90(16) . . ?
C1' C2' C11' 122.62(15) . . ?
C3' C2' C11' 117.48(15) . . ?
O2A C11' O1A 119.3(12) . . ?
O2A C11' O2' 42.4(11) . . ?
O1A C11' O2' 103.6(9) . . ?
O2A C11' O1' 105.1(10) . . ?
O1A C11' O1' 48.3(10) . . ?
O2' C11' O1' 126.29(18) . . ?
O2A C11' C2' 119.4(9) . . ?
O1A C11' C2' 121.3(8) . . ?
O2' C11' C2' 117.20(17) . . ?
O1' C11' C2' 116.39(15) . . ?
C2 C1 C9 119.59(16) . . ?
C2 C1 C1' 122.32(15) . . ?
C9 C1 C1' 117.68(15) . . ?
H1 O5 H2 117.0(3) . . ?
O2 C11 O1 123.91(17) . . ?
O2 C11 C2 120.67(15) . . ?
O1 C11 C2 115.30(15) . . ?
C7 C8 C9 121.30(19) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8' C9' C10' 118.09(16) . . ?
C8' C9' C1' 122.45(16) . . ?
C10' C9' C1' 119.46(16) . . ?
C8 C9 C10 117.89(16) . . ?
C8 C9 C1 122.66(17) . . ?
C10 C9 C1 119.41(16) . . ?
C4' C10' C5' 121.85(19) . . ?
C4' C10' C9' 119.15(17) . . ?
C5' C10' C9' 118.98(18) . . ?
O4 C22 O3 121.66(17) . . ?
O4 C22 N1D 120.45(17) . . ?
O3 C22 N1D 117.89(17) . . ?
C4 C3 C2 121.30(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C10 C5 121.88(18) . . ?
C4 C10 C9 118.90(17) . . ?
C5 C10 C9 119.18(18) . . ?
C4' C3' C2' 121.26(17) . . ?
C4' C3' H3' 119.4 . . ?
C2' C3' H3' 119.4 . . ?
C7' C8' C9' 121.08(19) . . ?
C7' C8' H8' 119.5 . . ?
C9' C8' H8' 119.5 . . ?
C5 C6 C7 120.24(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
N1D C1D C6D 109.84(16) . . ?
N1D C1D C2D 113.07(16) . . ?
C6D C1D C2D 110.46(17) . . ?
N1D C1D H29 107.8 . . ?
C6D C1D H29 107.8 . . ?
C2D C1D H29 107.8 . . ?
C8 C7 C6 120.31(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C3' C4' C10' 120.52(17) . . ?
C3' C4' H4' 119.7 . . ?
C10' C4' H4' 119.7 . . ?
C3 C4 C10 120.78(18) . . ?
C3 C4 H4 119.6 . . ?
C10 C4 H4 119.6 . . ?
C8' C7' C6' 120.4(2) . . ?
C8' C7' H7' 119.8 . . ?
C6' C7' H7' 119.8 . . ?
C6' C5' C10' 120.8(2) . . ?
C6' C5' H5' 119.6 . . ?
C10' C5' H5' 119.6 . . ?
C6 C5 C10 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C5' C6' C7' 120.64(19) . . ?
C5' C6' H6' 119.7 . . ?
C7' C6' H6' 119.7 . . ?
C1A N1A H20 108(2) . . ?
C1A N1A H19 110(3) . . ?
H20 N1A H19 107(3) . . ?
C4D C5D C6D 112.24(18) . . ?
C4D C5D H5D1 109.2 . . ?
C6D C5D H5D1 109.2 . . ?
C4D C5D H5D2 109.2 . . ?
C6D C5D H5D2 109.2 . . ?
H5D1 C5D H5D2 107.9 . . ?
C1D C2D C3D 111.53(16) . . ?
C1D C2D H43A 109.3 . . ?
C3D C2D H43A 109.3 . . ?
C1D C2D H43B 109.3 . . ?
C3D C2D H43B 109.3 . . ?
H43A C2D H43B 108.0 . . ?
N1A C1A C6A 108.56(19) . . ?
N1A C1A C2A 108.1(2) . . ?
C6A C1A C2A 110.9(2) . . ?
N1A C1A H46 109.7 . . ?
C6A C1A H46 109.7 . . ?
C2A C1A H46 109.7 . . ?
C1D C6D C5D 111.96(18) . . ?
C1D C6D H6D2 109.2 . . ?
C5D C6D H6D2 109.2 . . ?
C1D C6D H6D1 109.2 . . ?
C5D C6D H6D1 109.2 . . ?
H6D2 C6D H6D1 107.9 . . ?
C5D C4D C3D 110.53(19) . . ?
C5D C4D H49A 109.5 . . ?
C3D C4D H49A 109.5 . . ?
C5D C4D H49B 109.5 . . ?
C3D C4D H49B 109.5 . . ?
H49A C4D H49B 108.1 . . ?
C2D C3D C4D 110.94(19) . . ?
C2D C3D H50A 109.5 . . ?
C4D C3D H50A 109.5 . . ?
C2D C3D H50B 109.5 . . ?
C4D C3D H50B 109.5 . . ?
H50A C3D H50B 108.0 . . ?
C1A C2A C3A 110.0(3) . . ?
C1A C2A H54A 109.7 . . ?
C3A C2A H54A 109.7 . . ?
C1A C2A H54B 109.7 . . ?
C3A C2A H54B 109.7 . . ?
H54A C2A H54B 108.2 . . ?
C1A C6A C5A 111.3(2) . . ?
C1A C6A H58A 109.4 . . ?
C5A C6A H58A 109.4 . . ?
C1A C6A H58B 109.4 . . ?
C5A C6A H58B 109.4 . . ?
H58A C6A H58B 108.0 . . ?
C4A C5A C6A 112.0(2) . . ?
C4A C5A H60A 109.2 . . ?
C6A C5A H60A 109.2 . . ?
C4A C5A H60B 109.2 . . ?
C6A C5A H60B 109.2 . . ?
H60A C5A H60B 107.9 . . ?
C2A C3A C4A 109.4(2) . . ?
C2A C3A H63A 109.8 . . ?
C4A C3A H63A 109.8 . . ?
C2A C3A H63B 109.8 . . ?
C4A C3A H63B 109.8 . . ?
H63A C3A H63B 108.2 . . ?
C5A C4A C3A 109.6(3) . . ?
C5A C4A H65A 109.8 . . ?
C3A C4A H65A 109.8 . . ?
C5A C4A H65B 109.8 . . ?
C3A C4A H65B 109.8 . . ?
H65A C4A H65B 108.2 . . ?
C1C N1C H15 109.9(13) . . ?
C1C N1C H17 110.8(16) . . ?
H15 N1C H17 101(2) . . ?
C1C N1C H16 109.6(16) . . ?
H15 N1C H16 109(2) . . ?
H17 N1C H16 116(2) . . ?
N1C C1C C2C 110.27(17) . . ?
N1C C1C C6C 110.96(16) . . ?
C2C C1C C6C 110.84(17) . . ?
N1C C1C H35 108.2 . . ?
C2C C1C H35 108.2 . . ?
C6C C1C H35 108.2 . . ?
C1C C6C C5C 110.45(19) . . ?
C1C C6C H41A 109.6 . . ?
C5C C6C H41A 109.6 . . ?
C1C C6C H41B 109.6 . . ?
C5C C6C H41B 109.6 . . ?
H41A C6C H41B 108.1 . . ?
C1C C2C C3C 110.49(19) . . ?
C1C C2C H45A 109.6 . . ?
C3C C2C H45A 109.6 . . ?
C1C C2C H45B 109.6 . . ?
C3C C2C H45B 109.6 . . ?
H45A C2C H45B 108.1 . . ?
C4C C3C C2C 111.0(2) . . ?
C4C C3C H51A 109.4 . . ?
C2C C3C H51A 109.4 . . ?
C4C C3C H55B 109.4 . . ?
C2C C3C H55B 109.4 . . ?
H51A C3C H55B 108.0 . . ?
C5C C4C C3C 111.4(2) . . ?
C5C C4C H55A 109.3 . . ?
C3C C4C H55A 109.3 . . ?
C5C C4C H4D2 109.3 . . ?
C3C C4C H4D2 109.3 . . ?
H55A C4C H4D2 108.0 . . ?
C4C C5C C6C 111.5(2) . . ?
C4C C5C H56A 109.3 . . ?
C6C C5C H56A 109.3 . . ?
C4C C5C H56B 109.3 . . ?
C6C C5C H56B 109.3 . . ?
H56A C5C H56B 108.0 . . ?
C1B N1B H12 109.1(15) . . ?
C1B N1B H14 110.4(16) . . ?
H12 N1B H14 105(2) . . ?
C1B N1B H13 109.8(13) . . ?
H12 N1B H13 111(2) . . ?
H14 N1B H13 111(2) . . ?
N1B C1B C2B 109.98(17) . . ?
N1B C1B C6B 110.51(16) . . ?
C2B C1B C6B 111.88(17) . . ?
N1B C1B H26 108.1 . . ?
C2B C1B H26 108.1 . . ?
C6B C1B H26 108.1 . . ?
C1B C6B C5B 109.94(17) . . ?
C1B C6B H40A 109.7 . . ?
C5B C6B H40A 109.7 . . ?
C1B C6B H40B 109.7 . . ?
C5B C6B H40B 109.7 . . ?
H40A C6B H40B 108.2 . . ?
C1B C2B C3B 110.66(19) . . ?
C1B C2B H42A 109.5 . . ?
C3B C2B H42A 109.5 . . ?
C1B C2B H42B 109.5 . . ?
C3B C2B H42B 109.5 . . ?
H42A C2B H42B 108.1 . . ?
C4B C5B C6B 111.9(2) . . ?
C4B C5B H44A 109.2 . . ?
C6B C5B H44A 109.2 . . ?
C4B C5B H44B 109.2 . . ?
C6B C5B H44B 109.2 . . ?
H44A C5B H44B 107.9 . . ?
C3B C4B C5B 111.5(2) . . ?
C3B C4B H52A 109.3 . . ?
C5B C4B H52A 109.3 . . ?
C3B C4B H52B 109.3 . . ?
C5B C4B H52B 109.3 . . ?
H52A C4B H52B 108.0 . . ?
C4B C3B C2B 110.9(2) . . ?
C4B C3B H57A 109.5 . . ?
C2B C3B H57A 109.5 . . ?
C4B C3B H57B 109.5 . . ?
C2B C3B H57B 109.5 . . ?
H57A C3B H57B 108.0 . . ?
C1E C6E C5E 111.4(4) . . ?
C1E C6E H53A 109.3 . . ?
C5E C6E H53A 109.3 . . ?
C1E C6E H6E1 109.3 . . ?
C5E C6E H6E1 109.3 . . ?
H53A C6E H6E1 108.0 . . ?
C3E C2E C1E 110.1(5) . . ?
C3E C2E H59A 109.6 . . ?
C1E C2E H59A 109.6 . . ?
C3E C2E H59B 109.6 . . ?
C1E C2E H59B 109.6 . . ?
H59A C2E H59B 108.2 . . ?
C3E C4E C5E 110.0(6) . . ?
C3E C4E H61A 109.7 . . ?
C5E C4E H61A 109.7 . . ?
C3E C4E H61B 109.7 . . ?
C5E C4E H61B 109.7 . . ?
H61A C4E H61B 108.2 . . ?
C4E C3E C2E 113.3(6) . . ?
C4E C3E H62A 108.9 . . ?
C2E C3E H62A 108.9 . . ?
C4E C3E H62B 108.9 . . ?
C2E C3E H62B 108.9 . . ?
H62A C3E H62B 107.7 . . ?
C6E C5E C4E 110.6(4) . . ?
C6E C5E H64A 109.5 . . ?
C4E C5E H64A 109.5 . . ?
C6E C5E H64B 109.5 . . ?
C4E C5E H64B 109.5 . . ?
H64A C5E H64B 108.1 . . ?
N1E C1E C6E 111.8(4) . . ?
N1E C1E C2E 107.1(4) . . ?
C6E C1E C2E 112.1(3) . . ?
N1E C1E H1E 108.6 . . ?
C6E C1E H1E 108.6 . . ?
C2E C1E H1E 108.6 . . ?
C1F C2F C3F 110.5(16) . . ?
C1F C2F H2D1 109.5 . . ?
C3F C2F H2D1 109.5 . . ?
C1F C2F H2D2 109.5 . . ?
C3F C2F H2D2 109.5 . . ?
H2D1 C2F H2D2 108.1 . . ?
C5F C4F C3F 118.4(19) . . ?
C5F C4F H4F2 107.7 . . ?
C3F C4F H4F2 107.7 . . ?
C5F C4F H4F1 107.7 . . ?
C3F C4F H4F1 107.7 . . ?
H4F2 C4F H4F1 107.1 . . ?
C2F C3F C4F 106(2) . . ?
C2F C3F H3D1 110.5 . . ?
C4F C3F H3D1 110.5 . . ?
C2F C3F H3D2 110.5 . . ?
C4F C3F H3D2 110.5 . . ?
H3D1 C3F H3D2 108.7 . . ?
C4F C5F C6F 114.9(16) . . ?
C4F C5F H5E2 108.5 . . ?
C6F C5F H5E2 108.5 . . ?
C4F C5F H5E1 108.5 . . ?
C6F C5F H5E1 108.5 . . ?
H5E2 C5F H5E1 107.5 . . ?
C5F C6F C1F 111.4(17) . . ?
C5F C6F H6E2 109.3 . . ?
C1F C6F H6E2 109.3 . . ?
C5F C6F H18 109.3 . . ?
C1F C6F H18 109.3 . . ?
H6E2 C6F H18 108.0 . . ?
N9A C1F C2F 112.1(16) . . ?
N9A C1F C6F 97.6(16) . . ?
C2F C1F C6F 114.0(12) . . ?
N9A C1F H1D 110.9 . . ?
C2F C1F H1D 110.9 . . ?
C6F C1F H1D 110.9 . . ?
C1F N9A H11 109.5 . . ?
C1F N9A H9 109.5 . . ?
H11 N9A H9 109.5 . . ?
C1F N9A H10 109.5 . . ?
H11 N9A H10 109.5 . . ?
H9 N9A H10 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9' C1' C2' C3' -1.0(2) . . . . ?
C1 C1' C2' C3' 173.01(16) . . . . ?
C9' C1' C2' C11' 179.09(15) . . . . ?
C1 C1' C2' C11' -6.9(3) . . . . ?
C1' C2' C11' O2A -177.2(14) . . . . ?
C3' C2' C11' O2A 2.8(14) . . . . ?
C1' C2' C11' O1A 6.0(13) . . . . ?
C3' C2' C11' O1A -173.9(13) . . . . ?
C1' C2' C11' O2' 134.4(2) . . . . ?
C3' C2' C11' O2' -45.5(3) . . . . ?
C1' C2' C11' O1' -49.4(3) . . . . ?
C3' C2' C11' O1' 130.6(2) . . . . ?
C3 C2 C1 C9 0.8(2) . . . . ?
C11 C2 C1 C9 -175.96(14) . . . . ?
C3 C2 C1 C1' 173.27(15) . . . . ?
C11 C2 C1 C1' -3.5(2) . . . . ?
C2' C1' C1 C2 110.58(19) . . . . ?
C9' C1' C1 C2 -75.4(2) . . . . ?
C2' C1' C1 C9 -76.9(2) . . . . ?
C9' C1' C1 C9 97.21(18) . . . . ?
C1 C2 C11 O2 -64.2(2) . . . . ?
C3 C2 C11 O2 118.87(19) . . . . ?
C1 C2 C11 O1 119.77(18) . . . . ?
C3 C2 C11 O1 -57.2(2) . . . . ?
C2' C1' C9' C8' 177.09(16) . . . . ?
C1 C1' C9' C8' 2.9(2) . . . . ?
C2' C1' C9' C10' -2.4(2) . . . . ?
C1 C1' C9' C10' -176.63(15) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 C1 -177.27(17) . . . . ?
C2 C1 C9 C8 176.76(16) . . . . ?
C1' C1 C9 C8 4.0(2) . . . . ?
C2 C1 C9 C10 -0.9(2) . . . . ?
C1' C1 C9 C10 -173.64(15) . . . . ?
C8' C9' C10' C4' -176.09(17) . . . . ?
C1' C9' C10' C4' 3.4(3) . . . . ?
C8' C9' C10' C5' 2.5(3) . . . . ?
C1' C9' C10' C5' -178.02(16) . . . . ?
C1D N1D C22 O4 -5.3(3) . . . . ?
C1D N1D C22 O3 175.13(18) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C11 C2 C3 C4 177.25(17) . . . . ?
C8 C9 C10 C4 -177.88(17) . . . . ?
C1 C9 C10 C4 -0.1(3) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
C1 C9 C10 C5 177.68(16) . . . . ?
C1' C2' C3' C4' 3.4(3) . . . . ?
C11' C2' C3' C4' -176.62(17) . . . . ?
C10' C9' C8' C7' -2.1(3) . . . . ?
C1' C9' C8' C7' 178.45(18) . . . . ?
C22 N1D C1D C6D 148.0(2) . . . . ?
C22 N1D C1D C2D -88.1(2) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C2' C3' C4' C10' -2.4(3) . . . . ?
C5' C10' C4' C3' -179.56(19) . . . . ?
C9' C10' C4' C3' -1.0(3) . . . . ?
C2 C3 C4 C10 -1.2(3) . . . . ?
C5 C10 C4 C3 -176.57(19) . . . . ?
C9 C10 C4 C3 1.2(3) . . . . ?
C9' C8' C7' C6' 0.0(3) . . . . ?
C4' C10' C5' C6' 177.6(2) . . . . ?
C9' C10' C5' C6' -0.9(3) . . . . ?
C7 C6 C5 C10 1.1(3) . . . . ?
C4 C10 C5 C6 177.1(2) . . . . ?
C9 C10 C5 C6 -0.7(3) . . . . ?
C10' C5' C6' C7' -1.2(3) . . . . ?
C8' C7' C6' C5' 1.6(3) . . . . ?
N1D C1D C2D C3D -179.18(17) . . . . ?
C6D C1D C2D C3D -55.6(2) . . . . ?
N1D C1D C6D C5D 179.46(17) . . . . ?
C2D C1D C6D C5D 54.1(2) . . . . ?
C4D C5D C6D C1D -54.4(3) . . . . ?
C6D C5D C4D C3D 54.7(3) . . . . ?
C1D C2D C3D C4D 57.0(2) . . . . ?
C5D C4D C3D C2D -55.8(3) . . . . ?
N1A C1A C2A C3A 178.3(2) . . . . ?
C6A C1A C2A C3A 59.4(3) . . . . ?
N1A C1A C6A C5A -173.7(2) . . . . ?
C2A C1A C6A C5A -55.1(3) . . . . ?
C1A C6A C5A C4A 53.6(3) . . . . ?
C1A C2A C3A C4A -61.1(3) . . . . ?
C6A C5A C4A C3A -55.2(4) . . . . ?
C2A C3A C4A C5A 58.7(4) . . . . ?
N1C C1C C6C C5C 179.48(18) . . . . ?
C2C C1C C6C C5C -57.6(2) . . . . ?
N1C C1C C2C C3C -178.54(18) . . . . ?
C6C C1C C2C C3C 58.2(3) . . . . ?
C1C C2C C3C C4C -56.4(3) . . . . ?
C2C C3C C4C C5C 54.6(3) . . . . ?
C3C C4C C5C C6C -54.4(3) . . . . ?
C1C C6C C5C C4C 55.7(3) . . . . ?
N1B C1B C6B C5B 179.35(17) . . . . ?
C2B C1B C6B C5B 56.4(2) . . . . ?
N1B C1B C2B C3B 179.48(18) . . . . ?
C6B C1B C2B C3B -57.3(2) . . . . ?
C1B C6B C5B C4B -54.8(3) . . . . ?
C6B C5B C4B C3B 54.8(3) . . . . ?
C5B C4B C3B C2B -54.7(3) . . . . ?
C1B C2B C3B C4B 55.9(3) . . . . ?
C5E C4E C3E C2E -55.8(9) . . . . ?
C1E C2E C3E C4E 54.3(9) . . . . ?
C1E C6E C5E C4E -56.7(6) . . . . ?
C3E C4E C5E C6E 55.9(8) . . . . ?
C5E C6E C1E N1E 176.1(4) . . . . ?
C5E C6E C1E C2E 55.8(4) . . . . ?
C3E C2E C1E N1E -176.5(5) . . . . ?
C3E C2E C1E C6E -53.5(6) . . . . ?
C1F C2F C3F C4F -54(3) . . . . ?
C5F C4F C3F C2F 51(3) . . . . ?
C3F C4F C5F C6F -47(3) . . . . ?
C4F C5F C6F C1F 44(3) . . . . ?
C3F C2F C1F N9A 169(2) . . . . ?
C3F C2F C1F C6F 59(2) . . . . ?
C5F C6F C1F N9A -169.8(17) . . . . ?
C5F C6F C1F C2F -51.5(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 969505'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
dicyclohexylammonium-1,1'-binaphthyl-2,2'-dicarboxylate methanol hydrate  
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H66 N2 O6'
_chemical_formula_weight         755.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.970(3)
_cell_length_b                   19.964(4)
_cell_length_c                   15.127(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.88(3)
_cell_angle_gamma                90.00
_cell_volume                     4179.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18734
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 none 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ scans and ω scans'
_diffrn_reflns_number            18734
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.47
_reflns_number_total             9505
_reflns_number_gt                6530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9505
_refine_ls_number_parameters     504
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O 0.48255(6) 0.21698(4) 0.90039(5) 0.0296(2) Uani 1 1 d . . .
O2 O 0.25971(6) 0.22349(4) 0.69886(5) 0.0304(2) Uani 1 1 d . . .
O2' O 0.45812(7) 0.17698(4) 1.03308(6) 0.0346(2) Uani 1 1 d . . .
O1 O 0.28545(6) 0.18455(4) 0.56624(5) 0.0319(2) Uani 1 1 d . . .
N1B N 0.06049(7) 0.24836(5) 0.66509(6) 0.0234(2) Uani 1 1 d . . .
N1A N 0.17534(7) 0.25110(5) 0.42646(6) 0.0247(2) Uani 1 1 d . . .
C1 C 0.40935(8) 0.12088(5) 0.76832(7) 0.0207(2) Uani 1 1 d . . .
C10 C 0.56573(8) 0.07588(6) 0.73686(8) 0.0250(3) Uani 1 1 d . . .
C2 C 0.40068(8) 0.15606(5) 0.68872(7) 0.0220(2) Uani 1 1 d . . .
C4 C 0.55795(8) 0.11729(6) 0.66049(8) 0.0268(3) Uani 1 1 d . . .
H4 H 0.6096 0.1189 0.6257 0.032 Uiso 1 1 calc R . .
C9' C 0.24798(8) 0.07919(5) 0.79926(8) 0.0237(3) Uani 1 1 d . . .
C8' C 0.24036(9) 0.03951(6) 0.72091(8) 0.0308(3) Uani 1 1 d . . .
H8' H 0.2884 0.0432 0.6824 0.037 Uiso 1 1 calc R . .
C10' C 0.17367(8) 0.07469(6) 0.85417(8) 0.0270(3) Uani 1 1 d . . .
C11 C 0.30802(8) 0.19132(5) 0.64970(8) 0.0237(3) Uani 1 1 d . . .
C3 C 0.47734(8) 0.15489(6) 0.63622(8) 0.0253(3) Uani 1 1 d . . .
H3 H 0.4723 0.1808 0.5831 0.030 Uiso 1 1 calc R . .
C16 C 0.01226(9) 0.18087(6) 0.65423(8) 0.0267(3) Uani 1 1 d . . .
H16 H 0.0408 0.1509 0.7040 0.032 Uiso 1 1 calc R . .
C1' C 0.33157(8) 0.11974(5) 0.82698(7) 0.0213(2) Uani 1 1 d . . .
C3' C 0.26776(9) 0.14352(6) 0.96473(8) 0.0272(3) Uani 1 1 d . . .
H3' H 0.2755 0.1642 1.0218 0.033 Uiso 1 1 calc R . .
C11' C 0.43519(8) 0.18409(5) 0.95065(8) 0.0242(3) Uani 1 1 d . . .
C8 C 0.49661(9) 0.03238(6) 0.86485(8) 0.0285(3) Uani 1 1 d . . .
H8 H 0.4475 0.0330 0.9025 0.034 Uiso 1 1 calc R . .
C2' C 0.34262(8) 0.14932(5) 0.91045(8) 0.0225(2) Uani 1 1 d . . .
C9 C 0.49091(8) 0.07749(5) 0.79164(7) 0.0226(2) Uani 1 1 d . . .
C7B C 0.04516(9) 0.28914(6) 0.74561(7) 0.0260(3) Uani 1 1 d . . .
H7B H -0.0258 0.2964 0.7444 0.031 Uiso 1 1 calc R . .
C5 C 0.64426(9) 0.03086(6) 0.75861(9) 0.0328(3) Uani 1 1 d . . .
H5 H 0.6959 0.0308 0.7237 0.039 Uiso 1 1 calc R . .
C4' C 0.18527(9) 0.10902(6) 0.93673(8) 0.0298(3) Uani 1 1 d . . .
H4' H 0.1349 0.1080 0.9730 0.036 Uiso 1 1 calc R . .
C1A C 0.18836(9) 0.20518(6) 0.35051(8) 0.0265(3) Uani 1 1 d . . .
H1A H 0.2590 0.1962 0.3522 0.032 Uiso 1 1 calc R . .
C2A C 0.13771(9) 0.13862(6) 0.36226(8) 0.0288(3) Uani 1 1 d . . .
H2A1 H 0.1630 0.1187 0.4207 0.035 Uiso 1 1 calc R . .
H2A2 H 0.0674 0.1461 0.3606 0.035 Uiso 1 1 calc R . .
C7A C 0.22564(9) 0.31788(6) 0.42898(8) 0.0282(3) Uani 1 1 d . . .
H7A H 0.1932 0.3463 0.3792 0.034 Uiso 1 1 calc R . .
O3 O 0.36300(7) 0.10358(5) 0.44663(6) 0.0474(3) Uani 1 1 d . . .
C8B C 0.09313(10) 0.35719(6) 0.73949(9) 0.0330(3) Uani 1 1 d . . .
H8B1 H 0.0655 0.3800 0.6837 0.040 Uiso 1 1 calc R . .
H8B2 H 0.1633 0.3512 0.7385 0.040 Uiso 1 1 calc R . .
C5' C 0.09319(9) 0.03234(6) 0.82682(9) 0.0357(3) Uani 1 1 d . . .
H5' H 0.0406 0.0315 0.8605 0.043 Uiso 1 1 calc R . .
C6A C 0.15121(10) 0.23681(6) 0.26090(8) 0.0338(3) Uani 1 1 d . . .
H6A1 H 0.1865 0.2790 0.2539 0.041 Uiso 1 1 calc R . .
H6A2 H 0.0818 0.2476 0.2586 0.041 Uiso 1 1 calc R . .
C5B C -0.01746(10) 0.08542(6) 0.54360(10) 0.0392(3) Uani 1 1 d . . .
H5B1 H -0.0059 0.0705 0.4836 0.047 Uiso 1 1 calc R . .
H5B2 H 0.0095 0.0511 0.5873 0.047 Uiso 1 1 calc R . .
C6B C 0.03400(9) 0.15194(6) 0.56574(8) 0.0302(3) Uani 1 1 d . . .
H6B1 H 0.0135 0.1844 0.5174 0.036 Uiso 1 1 calc R . .
H6B2 H 0.1046 0.1452 0.5687 0.036 Uiso 1 1 calc R . .
C3A C 0.15575(10) 0.09124(6) 0.28741(9) 0.0349(3) Uani 1 1 d . . .
H3A1 H 0.1231 0.0480 0.2947 0.042 Uiso 1 1 calc R . .
H3A2 H 0.2259 0.0826 0.2909 0.042 Uiso 1 1 calc R . .
C4A C 0.11804(10) 0.12101(8) 0.19649(9) 0.0415(3) Uani 1 1 d . . .
H4A1 H 0.0471 0.1266 0.1912 0.050 Uiso 1 1 calc R . .
H4A2 H 0.1323 0.0901 0.1488 0.050 Uiso 1 1 calc R . .
C2B C -0.09615(9) 0.18658(7) 0.65601(10) 0.0393(3) Uani 1 1 d . . .
H2B1 H -0.1238 0.2201 0.6115 0.047 Uiso 1 1 calc R . .
H2B2 H -0.1083 0.2019 0.7157 0.047 Uiso 1 1 calc R . .
C7 C 0.57168(10) -0.01206(6) 0.88218(9) 0.0353(3) Uani 1 1 d . . .
H7 H 0.5731 -0.0428 0.9303 0.042 Uiso 1 1 calc R . .
C12B C 0.08318(10) 0.25317(6) 0.83152(8) 0.0342(3) Uani 1 1 d . . .
H12A H 0.1526 0.2429 0.8322 0.041 Uiso 1 1 calc R . .
H12B H 0.0482 0.2103 0.8348 0.041 Uiso 1 1 calc R . .
C6' C 0.09047(10) -0.00700(7) 0.75290(10) 0.0426(4) Uani 1 1 d . . .
H6' H 0.0377 -0.0367 0.7373 0.051 Uiso 1 1 calc R . .
C6 C 0.64648(10) -0.01215(7) 0.82882(9) 0.0378(3) Uani 1 1 d . . .
H6 H 0.6990 -0.0424 0.8418 0.045 Uiso 1 1 calc R . .
C9B C 0.07641(12) 0.39978(7) 0.81989(9) 0.0428(3) Uani 1 1 d . . .
H9B1 H 0.1088 0.4437 0.8167 0.051 Uiso 1 1 calc R . .
H9B2 H 0.0063 0.4080 0.8184 0.051 Uiso 1 1 calc R . .
C12A C 0.21407(10) 0.35131(6) 0.51756(9) 0.0327(3) Uani 1 1 d . . .
H12C H 0.2397 0.3212 0.5673 0.039 Uiso 1 1 calc R . .
H12D H 0.1446 0.3588 0.5207 0.039 Uiso 1 1 calc R . .
C5A C 0.16521(11) 0.18880(7) 0.18479(9) 0.0414(3) Uani 1 1 d . . .
H5A1 H 0.1367 0.2088 0.1273 0.050 Uiso 1 1 calc R . .
H5A2 H 0.2352 0.1823 0.1830 0.050 Uiso 1 1 calc R . .
C8A C 0.33147(10) 0.30993(7) 0.41765(10) 0.0384(3) Uani 1 1 d . . .
H8A1 H 0.3366 0.2903 0.3584 0.046 Uiso 1 1 calc R . .
H8A2 H 0.3634 0.2791 0.4638 0.046 Uiso 1 1 calc R . .
C10B C 0.11546(12) 0.36526(8) 0.90656(9) 0.0486(4) Uani 1 1 d . . .
H10A H 0.1017 0.3931 0.9575 0.058 Uiso 1 1 calc R . .
H10B H 0.1864 0.3604 0.9103 0.058 Uiso 1 1 calc R . .
C7' C 0.16502(11) -0.00401(7) 0.69966(10) 0.0415(3) Uani 1 1 d . . .
H7' H 0.1632 -0.0322 0.6489 0.050 Uiso 1 1 calc R . .
C11A C 0.26735(11) 0.41818(7) 0.52805(10) 0.0437(4) Uani 1 1 d . . .
H11A H 0.2352 0.4505 0.4841 0.052 Uiso 1 1 calc R . .
H11B H 0.2640 0.4363 0.5885 0.052 Uiso 1 1 calc R . .
C11B C 0.06982(12) 0.29672(7) 0.91236(9) 0.0416(3) Uani 1 1 d . . .
H11C H 0.0000 0.3021 0.9157 0.050 Uiso 1 1 calc R . .
H11D H 0.0995 0.2740 0.9676 0.050 Uiso 1 1 calc R . .
C3B C -0.14507(12) 0.11895(8) 0.63502(12) 0.0549(4) Uani 1 1 d . . .
H3B1 H -0.1215 0.0866 0.6827 0.066 Uiso 1 1 calc R . .
H3B2 H -0.2157 0.1240 0.6341 0.066 Uiso 1 1 calc R . .
C10A C 0.37237(12) 0.41069(9) 0.51436(12) 0.0590(5) Uani 1 1 d . . .
H10C H 0.4031 0.4554 0.5165 0.071 Uiso 1 1 calc R . .
H10D H 0.4067 0.3834 0.5634 0.071 Uiso 1 1 calc R . .
C9A C 0.38195(12) 0.37774(8) 0.42600(12) 0.0555(4) Uani 1 1 d . . .
H9A1 H 0.4512 0.3717 0.4206 0.067 Uiso 1 1 calc R . .
H9A2 H 0.3534 0.4072 0.3767 0.067 Uiso 1 1 calc R . .
C4B C -0.12489(11) 0.09155(8) 0.54566(11) 0.0524(4) Uani 1 1 d . . .
H4B1 H -0.1556 0.0470 0.5354 0.063 Uiso 1 1 calc R . .
H4B2 H -0.1534 0.1218 0.4972 0.063 Uiso 1 1 calc R . .
O4 O 0.37732(9) 0.32263(6) 0.80743(9) 0.0800(5) Uani 1 1 d . . .
C1C C 0.36983(13) 0.03729(7) 0.47730(12) 0.0587(4) Uani 1 1 d . . .
H1C1 H 0.4108 0.0356 0.5353 0.088 Uiso 1 1 calc R . .
H1C2 H 0.3982 0.0094 0.4344 0.088 Uiso 1 1 calc R . .
H1C3 H 0.3052 0.0205 0.4837 0.088 Uiso 1 1 calc R . .
H1' H 0.0357 0.2718 0.6150 0.036(4) Uiso 1 1 d R . .
H2 H 0.2011 0.2297 0.4784 0.038(4) Uiso 1 1 d R . .
H2' H 0.1261 0.2419 0.6690 0.031(3) Uiso 1 1 d R . .
H1 H 0.1101 0.2603 0.4242 0.044(4) Uiso 1 1 d R . .
H1C H 0.3448 0.1317 0.4939 0.090(7) Uiso 1 1 d R . .
H2D H 0.4133 0.2893 0.8360 0.107(8) Uiso 1 1 d R . .
H1D H 0.3347 0.2955 0.7638 0.146(11) Uiso 1 1 d R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1' C11' 1.2591(14) . ?
O2 C11 1.2485(14) . ?
O2' C11' 1.2522(14) . ?
O1 C11 1.2659(14) . ?
N1B C7B 1.5047(15) . ?
N1B C16 1.5053(15) . ?
N1B H1' 0.9170 . ?
N1B H2' 0.9196 . ?
N1A C1A 1.5002(15) . ?
N1A C7A 1.5051(15) . ?
N1A H2 0.9224 . ?
N1A H1 0.9265 . ?
C1 C2 1.3849(16) . ?
C1 C9 1.4363(16) . ?
C1 C1' 1.4944(16) . ?
C10 C4 1.4125(17) . ?
C10 C9 1.4205(16) . ?
C10 C5 1.4215(17) . ?
C2 C3 1.4182(16) . ?
C2 C11 1.5199(16) . ?
C4 C3 1.3613(17) . ?
C4 H4 0.9500 . ?
C9' C8' 1.4175(17) . ?
C9' C10' 1.4185(17) . ?
C9' C1' 1.4354(16) . ?
C8' C7' 1.3686(18) . ?
C8' H8' 0.9500 . ?
C10' C4' 1.4143(18) . ?
C10' C5' 1.4222(17) . ?
C3 H3 0.9500 . ?
C16 C2B 1.5227(18) . ?
C16 C6B 1.5263(17) . ?
C16 H16 1.0000 . ?
C1' C2' 1.3832(16) . ?
C3' C4' 1.3595(18) . ?
C3' C2' 1.4201(16) . ?
C3' H3' 0.9500 . ?
C11' C2' 1.5194(16) . ?
C8 C7 1.3712(17) . ?
C8 C9 1.4211(16) . ?
C8 H8 0.9500 . ?
C7B C12B 1.5157(17) . ?
C7B C8B 1.5232(17) . ?
C7B H7B 1.0000 . ?
C5 C6 1.3629(19) . ?
C5 H5 0.9500 . ?
C4' H4' 0.9500 . ?
C1A C6A 1.5208(17) . ?
C1A C2A 1.5273(17) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.5228(17) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C7A C8A 1.5199(18) . ?
C7A C12A 1.5253(17) . ?
C7A H7A 1.0000 . ?
O3 C1C 1.4013(19) . ?
O3 H1C 0.9695 . ?
C8B C9B 1.5280(18) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C5' C6' 1.363(2) . ?
C5' H5' 0.9500 . ?
C6A C5A 1.5311(19) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C5B C4B 1.510(2) . ?
C5B C6B 1.5254(18) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C3A C4A 1.5245(19) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.526(2) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C2B C3B 1.527(2) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C7 C6 1.4053(19) . ?
C7 H7 0.9500 . ?
C12B C11B 1.5326(18) . ?
C12B H12A 0.9900 . ?
C12B H12B 0.9900 . ?
C6' C7' 1.402(2) . ?
C6' H6' 0.9500 . ?
C6 H6 0.9500 . ?
C9B C10B 1.515(2) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C12A C11A 1.5261(19) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C8A C9A 1.524(2) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C10B C11B 1.517(2) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C7' H7' 0.9500 . ?
C11A C10A 1.517(2) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C3B C4B 1.520(2) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C10A C9A 1.512(2) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
O4 H2D 0.9077 . ?
O4 H1D 0.9875 . ?
C1C H1C1 0.9800 . ?
C1C H1C2 0.9800 . ?
C1C H1C3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7B N1B C16 117.48(9) . . ?
C7B N1B H1' 108.3 . . ?
C16 N1B H1' 104.7 . . ?
C7B N1B H2' 106.0 . . ?
C16 N1B H2' 108.0 . . ?
H1' N1B H2' 112.6 . . ?
C1A N1A C7A 117.10(9) . . ?
C1A N1A H2 107.1 . . ?
C7A N1A H2 105.2 . . ?
C1A N1A H1 108.4 . . ?
C7A N1A H1 106.2 . . ?
H2 N1A H1 112.9 . . ?
C2 C1 C9 119.43(10) . . ?
C2 C1 C1' 122.68(10) . . ?
C9 C1 C1' 117.51(10) . . ?
C4 C10 C9 118.92(10) . . ?
C4 C10 C5 121.99(11) . . ?
C9 C10 C5 119.04(11) . . ?
C1 C2 C3 119.72(10) . . ?
C1 C2 C11 122.75(10) . . ?
C3 C2 C11 117.28(10) . . ?
C3 C4 C10 120.76(11) . . ?
C3 C4 H4 119.6 . . ?
C10 C4 H4 119.6 . . ?
C8' C9' C10' 118.49(11) . . ?
C8' C9' C1' 121.63(11) . . ?
C10' C9' C1' 119.74(10) . . ?
C7' C8' C9' 121.22(12) . . ?
C7' C8' H8' 119.4 . . ?
C9' C8' H8' 119.4 . . ?
C4' C10' C9' 118.81(11) . . ?
C4' C10' C5' 122.36(12) . . ?
C9' C10' C5' 118.70(11) . . ?
O2 C11 O1 124.60(11) . . ?
O2 C11 C2 120.53(10) . . ?
O1 C11 C2 114.86(10) . . ?
C4 C3 C2 121.22(11) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
N1B C16 C2B 111.25(10) . . ?
N1B C16 C6B 107.13(9) . . ?
C2B C16 C6B 111.21(11) . . ?
N1B C16 H16 109.1 . . ?
C2B C16 H16 109.1 . . ?
C6B C16 H16 109.1 . . ?
C2' C1' C9' 119.47(10) . . ?
C2' C1' C1 122.43(10) . . ?
C9' C1' C1 117.63(10) . . ?
C4' C3' C2' 121.41(11) . . ?
C4' C3' H3' 119.3 . . ?
C2' C3' H3' 119.3 . . ?
O2' C11' O1' 125.21(11) . . ?
O2' C11' C2' 115.74(10) . . ?
O1' C11' C2' 119.04(10) . . ?
C7 C8 C9 121.24(12) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C1' C2' C3' 119.61(11) . . ?
C1' C2' C11' 122.88(10) . . ?
C3' C2' C11' 117.36(10) . . ?
C10 C9 C8 118.24(10) . . ?
C10 C9 C1 119.52(10) . . ?
C8 C9 C1 122.10(10) . . ?
N1B C7B C12B 111.45(9) . . ?
N1B C7B C8B 108.71(9) . . ?
C12B C7B C8B 111.67(10) . . ?
N1B C7B H7B 108.3 . . ?
C12B C7B H7B 108.3 . . ?
C8B C7B H7B 108.3 . . ?
C6 C5 C10 120.88(12) . . ?
C6 C5 H5 119.6 . . ?
C10 C5 H5 119.6 . . ?
C3' C4' C10' 120.69(11) . . ?
C3' C4' H4' 119.7 . . ?
C10' C4' H4' 119.7 . . ?
N1A C1A C6A 111.51(9) . . ?
N1A C1A C2A 109.62(9) . . ?
C6A C1A C2A 110.98(10) . . ?
N1A C1A H1A 108.2 . . ?
C6A C1A H1A 108.2 . . ?
C2A C1A H1A 108.2 . . ?
C3A C2A C1A 109.11(10) . . ?
C3A C2A H2A1 109.9 . . ?
C1A C2A H2A1 109.9 . . ?
C3A C2A H2A2 109.9 . . ?
C1A C2A H2A2 109.9 . . ?
H2A1 C2A H2A2 108.3 . . ?
N1A C7A C8A 111.26(10) . . ?
N1A C7A C12A 107.73(10) . . ?
C8A C7A C12A 111.51(11) . . ?
N1A C7A H7A 108.8 . . ?
C8A C7A H7A 108.8 . . ?
C12A C7A H7A 108.8 . . ?
C1C O3 H1C 108.4 . . ?
C7B C8B C9B 109.36(11) . . ?
C7B C8B H8B1 109.8 . . ?
C9B C8B H8B1 109.8 . . ?
C7B C8B H8B2 109.8 . . ?
C9B C8B H8B2 109.8 . . ?
H8B1 C8B H8B2 108.3 . . ?
C6' C5' C10' 120.89(12) . . ?
C6' C5' H5' 119.6 . . ?
C10' C5' H5' 119.6 . . ?
C1A C6A C5A 110.32(10) . . ?
C1A C6A H6A1 109.6 . . ?
C5A C6A H6A1 109.6 . . ?
C1A C6A H6A2 109.6 . . ?
C5A C6A H6A2 109.6 . . ?
H6A1 C6A H6A2 108.1 . . ?
C4B C5B C6B 111.39(11) . . ?
C4B C5B H5B1 109.3 . . ?
C6B C5B H5B1 109.3 . . ?
C4B C5B H5B2 109.3 . . ?
C6B C5B H5B2 109.3 . . ?
H5B1 C5B H5B2 108.0 . . ?
C5B C6B C16 112.18(11) . . ?
C5B C6B H6B1 109.2 . . ?
C16 C6B H6B1 109.2 . . ?
C5B C6B H6B2 109.2 . . ?
C16 C6B H6B2 109.2 . . ?
H6B1 C6B H6B2 107.9 . . ?
C2A C3A C4A 110.90(11) . . ?
C2A C3A H3A1 109.5 . . ?
C4A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
C4A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 108.0 . . ?
C3A C4A C5A 110.43(11) . . ?
C3A C4A H4A1 109.6 . . ?
C5A C4A H4A1 109.6 . . ?
C3A C4A H4A2 109.6 . . ?
C5A C4A H4A2 109.6 . . ?
H4A1 C4A H4A2 108.1 . . ?
C16 C2B C3B 110.37(12) . . ?
C16 C2B H2B1 109.6 . . ?
C3B C2B H2B1 109.6 . . ?
C16 C2B H2B2 109.6 . . ?
C3B C2B H2B2 109.6 . . ?
H2B1 C2B H2B2 108.1 . . ?
C8 C7 C6 120.03(12) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7B C12B C11B 110.41(10) . . ?
C7B C12B H12A 109.6 . . ?
C11B C12B H12A 109.6 . . ?
C7B C12B H12B 109.6 . . ?
C11B C12B H12B 109.6 . . ?
H12A C12B H12B 108.1 . . ?
C5' C6' C7' 120.48(12) . . ?
C5' C6' H6' 119.8 . . ?
C7' C6' H6' 119.8 . . ?
C5 C6 C7 120.50(12) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C10B C9B C8B 111.06(12) . . ?
C10B C9B H9B1 109.4 . . ?
C8B C9B H9B1 109.4 . . ?
C10B C9B H9B2 109.4 . . ?
C8B C9B H9B2 109.4 . . ?
H9B1 C9B H9B2 108.0 . . ?
C7A C12A C11A 111.42(11) . . ?
C7A C12A H12C 109.3 . . ?
C11A C12A H12C 109.3 . . ?
C7A C12A H12D 109.3 . . ?
C11A C12A H12D 109.3 . . ?
H12C C12A H12D 108.0 . . ?
C4A C5A C6A 111.48(11) . . ?
C4A C5A H5A1 109.3 . . ?
C6A C5A H5A1 109.3 . . ?
C4A C5A H5A2 109.3 . . ?
C6A C5A H5A2 109.3 . . ?
H5A1 C5A H5A2 108.0 . . ?
C7A C8A C9A 110.13(12) . . ?
C7A C8A H8A1 109.6 . . ?
C9A C8A H8A1 109.6 . . ?
C7A C8A H8A2 109.6 . . ?
C9A C8A H8A2 109.6 . . ?
H8A1 C8A H8A2 108.1 . . ?
C9B C10B C11B 110.86(12) . . ?
C9B C10B H10A 109.5 . . ?
C11B C10B H10A 109.5 . . ?
C9B C10B H10B 109.5 . . ?
C11B C10B H10B 109.5 . . ?
H10A C10B H10B 108.1 . . ?
C8' C7' C6' 119.99(13) . . ?
C8' C7' H7' 120.0 . . ?
C6' C7' H7' 120.0 . . ?
C10A C11A C12A 111.52(12) . . ?
C10A C11A H11A 109.3 . . ?
C12A C11A H11A 109.3 . . ?
C10A C11A H11B 109.3 . . ?
C12A C11A H11B 109.3 . . ?
H11A C11A H11B 108.0 . . ?
C10B C11B C12B 111.55(12) . . ?
C10B C11B H11C 109.3 . . ?
C12B C11B H11C 109.3 . . ?
C10B C11B H11D 109.3 . . ?
C12B C11B H11D 109.3 . . ?
H11C C11B H11D 108.0 . . ?
C4B C3B C2B 111.76(13) . . ?
C4B C3B H3B1 109.3 . . ?
C2B C3B H3B1 109.3 . . ?
C4B C3B H3B2 109.3 . . ?
C2B C3B H3B2 109.3 . . ?
H3B1 C3B H3B2 107.9 . . ?
C9A C10A C11A 111.59(13) . . ?
C9A C10A H10C 109.3 . . ?
C11A C10A H10C 109.3 . . ?
C9A C10A H10D 109.3 . . ?
C11A C10A H10D 109.3 . . ?
H10C C10A H10D 108.0 . . ?
C10A C9A C8A 111.33(13) . . ?
C10A C9A H9A1 109.4 . . ?
C8A C9A H9A1 109.4 . . ?
C10A C9A H9A2 109.4 . . ?
C8A C9A H9A2 109.4 . . ?
H9A1 C9A H9A2 108.0 . . ?
C5B C4B C3B 110.70(13) . . ?
C5B C4B H4B1 109.5 . . ?
C3B C4B H4B1 109.5 . . ?
C5B C4B H4B2 109.5 . . ?
C3B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 108.1 . . ?
H2D O4 H1D 99.2 . . ?
O3 C1C H1C1 109.5 . . ?
O3 C1C H1C2 109.5 . . ?
H1C1 C1C H1C2 109.5 . . ?
O3 C1C H1C3 109.5 . . ?
H1C1 C1C H1C3 109.5 . . ?
H1C2 C1C H1C3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -7.15(16) . . . . ?
C1' C1 C2 C3 -179.91(10) . . . . ?
C9 C1 C2 C11 166.96(10) . . . . ?
C1' C1 C2 C11 -5.80(16) . . . . ?
C9 C10 C4 C3 -4.29(17) . . . . ?
C5 C10 C4 C3 173.28(11) . . . . ?
C10' C9' C8' C7' -2.20(18) . . . . ?
C1' C9' C8' C7' 173.44(12) . . . . ?
C8' C9' C10' C4' 173.89(10) . . . . ?
C1' C9' C10' C4' -1.84(16) . . . . ?
C8' C9' C10' C5' -2.07(16) . . . . ?
C1' C9' C10' C5' -177.80(10) . . . . ?
C1 C2 C11 O2 41.60(16) . . . . ?
C3 C2 C11 O2 -144.16(11) . . . . ?
C1 C2 C11 O1 -137.85(11) . . . . ?
C3 C2 C11 O1 36.40(14) . . . . ?
C10 C4 C3 C2 2.84(17) . . . . ?
C1 C2 C3 C4 3.01(17) . . . . ?
C11 C2 C3 C4 -171.42(10) . . . . ?
C7B N1B C16 C2B 55.00(13) . . . . ?
C7B N1B C16 C6B 176.74(9) . . . . ?
C8' C9' C1' C2' -170.01(11) . . . . ?
C10' C9' C1' C2' 5.58(16) . . . . ?
C8' C9' C1' C1 2.30(16) . . . . ?
C10' C9' C1' C1 177.89(10) . . . . ?
C2 C1 C1' C2' -112.61(13) . . . . ?
C9 C1 C1' C2' 74.50(14) . . . . ?
C2 C1 C1' C9' 75.32(13) . . . . ?
C9 C1 C1' C9' -97.57(13) . . . . ?
C9' C1' C2' C3' -4.89(16) . . . . ?
C1 C1' C2' C3' -176.82(10) . . . . ?
C9' C1' C2' C11' 170.52(10) . . . . ?
C1 C1' C2' C11' -1.40(16) . . . . ?
C4' C3' C2' C1' 0.46(17) . . . . ?
C4' C3' C2' C11' -175.21(10) . . . . ?
O2' C11' C2' C1' -143.25(11) . . . . ?
O1' C11' C2' C1' 36.53(16) . . . . ?
O2' C11' C2' C3' 32.26(15) . . . . ?
O1' C11' C2' C3' -147.96(11) . . . . ?
C4 C10 C9 C8 175.92(10) . . . . ?
C5 C10 C9 C8 -1.73(16) . . . . ?
C4 C10 C9 C1 0.07(16) . . . . ?
C5 C10 C9 C1 -177.58(10) . . . . ?
C7 C8 C9 C10 -0.53(17) . . . . ?
C7 C8 C9 C1 175.21(11) . . . . ?
C2 C1 C9 C10 5.63(16) . . . . ?
C1' C1 C9 C10 178.76(10) . . . . ?
C2 C1 C9 C8 -170.05(10) . . . . ?
C1' C1 C9 C8 3.08(16) . . . . ?
C16 N1B C7B C12B 61.00(13) . . . . ?
C16 N1B C7B C8B -175.49(10) . . . . ?
C4 C10 C5 C6 -175.03(12) . . . . ?
C9 C10 C5 C6 2.54(18) . . . . ?
C2' C3' C4' C10' 3.38(18) . . . . ?
C9' C10' C4' C3' -2.61(17) . . . . ?
C5' C10' C4' C3' 173.20(11) . . . . ?
C7A N1A C1A C6A -60.24(13) . . . . ?
C7A N1A C1A C2A 176.46(9) . . . . ?
N1A C1A C2A C3A -177.14(9) . . . . ?
C6A C1A C2A C3A 59.25(13) . . . . ?
C1A N1A C7A C8A -49.65(14) . . . . ?
C1A N1A C7A C12A -172.15(10) . . . . ?
N1B C7B C8B C9B 178.84(10) . . . . ?
C12B C7B C8B C9B -57.79(14) . . . . ?
C4' C10' C5' C6' -171.04(12) . . . . ?
C9' C10' C5' C6' 4.77(18) . . . . ?
N1A C1A C6A C5A -179.86(10) . . . . ?
C2A C1A C6A C5A -57.34(14) . . . . ?
C4B C5B C6B C16 54.21(15) . . . . ?
N1B C16 C6B C5B -175.75(10) . . . . ?
C2B C16 C6B C5B -53.99(14) . . . . ?
C1A C2A C3A C4A -59.15(14) . . . . ?
C2A C3A C4A C5A 57.45(15) . . . . ?
N1B C16 C2B C3B 173.98(11) . . . . ?
C6B C16 C2B C3B 54.65(15) . . . . ?
C9 C8 C7 C6 2.04(19) . . . . ?
N1B C7B C12B C11B 178.09(10) . . . . ?
C8B C7B C12B C11B 56.28(15) . . . . ?
C10' C5' C6' C7' -3.2(2) . . . . ?
C10 C5 C6 C7 -1.1(2) . . . . ?
C8 C7 C6 C5 -1.3(2) . . . . ?
C7B C8B C9B C10B 57.87(16) . . . . ?
N1A C7A C12A C11A 177.17(10) . . . . ?
C8A C7A C12A C11A 54.82(14) . . . . ?
C3A C4A C5A C6A -55.15(15) . . . . ?
C1A C6A C5A C4A 55.15(15) . . . . ?
N1A C7A C8A C9A -176.64(11) . . . . ?
C12A C7A C8A C9A -56.34(15) . . . . ?
C8B C9B C10B C11B -57.18(17) . . . . ?
C9' C8' C7' C6' 3.9(2) . . . . ?
C5' C6' C7' C8' -1.2(2) . . . . ?
C7A C12A C11A C10A -53.27(16) . . . . ?
C9B C10B C11B C12B 55.33(17) . . . . ?
C7B C12B C11B C10B -54.65(16) . . . . ?
C16 C2B C3B C4B -56.71(18) . . . . ?
C12A C11A C10A C9A 54.16(19) . . . . ?
C11A C10A C9A C8A -56.3(2) . . . . ?
C7A C8A C9A C10A 57.06(18) . . . . ?
C6B C5B C4B C3B -55.11(17) . . . . ?
C2B C3B C4B C5B 57.02(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040

###END###

_database_code_depnum_ccdc_archive 'CCDC 969506'
